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| Novel chiral phosphine–oxazinane ligands in palladium-catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 42, Issue 29, 16 July 2001, Pages 4837-4839 Takashi Mino, Sosuke Hata, Kouji Ohtaka, Masami Sakamoto, Tsutomu Fujita | ||||
| A novel P-chirogenic phosphine ligand, (S,S)-1,2-bis-[(ferrocenyl)methylphosphino]ethane: synthesis and use in rhodium-catalyzed asymmetric hydrogenation and palladium-catalyzed asymmetric allylic alkylation Tetrahedron: Asymmetry, Volume 14, Issue 15, 1 August 2003, Pages 2171-2175 Nobuhiko Oohara, Kosuke Katagiri, Tsuneo Imamoto | ||||
| Palladium-catalyzed asymmetric allylic substitution using planar chiral hydrazone ligands Journal of Organometallic Chemistry, Volume 665, Issues 1-2, 3 January 2003, Pages 122-126 Takashi Mino, Teruhiro Ogawa, Masakazu Yamashita | ||||
| Modular chiral β-selenium-, sulfur-, and tellurium amides: synthesis and application in the palladium-catalyzed asymmetric allylic alkylation Tetrahedron, Volume 64, Issue 2, 7 January 2008, Pages 392-398 Fabrício Vargas, Jasquer A. Sehnem, Fabio Z. Galetto, Antonio L. Braga | ||||
| Synthesis of novel ferrocenylphosphine–amidine ligands and their application in Pd-catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 43, Issue 50, 9 December 2002, Pages 9179-9182 Xiangping Hu, Huilin Chen, Xinquan Hu, Huicong Dai, Changmin Bai, Junwei Wang, Zhuo Zheng | ||||
| Role of the planar chirality of imine–phosphine hybrid ligands bearing chromium tricarbonyl in the palladium-catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 41, Issue 26, 24 June 2000, Pages 5083-5087 Hye-Young Jang, Hwimin Seo, Jin Wook Han, Young Keun Chung | ||||
| Chiral β-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions Tetrahedron Letters, Volume 40, Issue 4, 22 January 1999, Pages 715-718 Kunio Hiroi, Yoshio Suzuki, Ryoko Kawagishi | ||||
| Palladium-catalyzed asymmetric allylic alkylation with an indenide Tetrahedron: Asymmetry, Volume 15, Issue 3, 9 February 2004, Pages 545-548 Tamio Hayashi, Toshimasa Suzuka, Atsushi Okada, Motoi Kawatsura | ||||
C24H20 Ee>99% (by preparation method) [α]D20=−74.3 (c 1.02, CHCl3) Source of chirality: chiral catalyst Absolute configuration: R
Dichloro-bis[1-{(R)-1,3-diphenyl-2-propenyl}indenyl]zirconium(IV)
C48H38Cl2Zr Ee>99% (by preparation method) [α]D20=+95.2 (c 0.96, CHCl3) Source of chirality: chiral catalyst Absolute configuration: R,R
| Palladium-catalyzed asymmetric allylic substitution using novel phosphino-ester (PHEST) ligands with 1,1′-binaphthyl skeleton Tetrahedron: Asymmetry, Volume 11, Issue 19, 6 October 2000, Pages 4009-4015 Hidehiko Kodama, Toshiji Taiji, Tetsuo Ohta, Isao Furukawa | ||||
| Synthesis of a novel type of chiral phosphinocarboxylic acids. The phosphine-palladium complexes catalyzed asymmetric allylic alkylation Tetrahedron: Asymmetry, Volume 2, Issue 7, 1991, Pages 667-682 Yoshiharu Okada, Toru Minami, Yasuo Umezu, Shinji Nishikawa, Ryoji Mori, Yutaka Nakayama | ||||
C17H17O2P (−)-Form: optical PURITY=96 %ee [α]D=−90.1 (c 6.3, CH2Cl2) (+)-Form: optical PURITY=92 %ee [α]D=86.5 (c 2.2, CH2Cl2)
trans-[2-(Diphenylphosphino)cyclobutyl]acetic acid
C18H19O2P (+)-Form: optical PURITY=>99 %ee [α]D=24.1 (c 1.6, CH2Cl2)
trans-(2-Diphenylphosphino)cyclopentanecarboxytic acid
C18H19O2P (−)-Form: optical PURITY=83 %ee [α]D=−29.6 (c 1.8, CH2Cl2) (+)-Form: optical PURITY=95 %ee [α]D=31.4 (c 1.0, CH2Cl2)
trans-[2-(Diphenylphosphino)cyclopentyl]acetic acid
C18H19O2P (−)-Form: optical PURITY=94 %ee [α]D=−2.69 (c 1.0, CH2Cl2) (+)-Form: optical PURITY=97 %ee [α]D=6.79 (c 1.0, CH2Cl2)
| The first synthesis of chiral phosphinocarboxylic acid ligands, trans-2-(diphenylphosphino)cycloalkanecarboxylic acids. The phosphine-palladium complexes catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 31, Issue 27, 1990, Pages 3905-3908 Yoshiharu Okada, Toru Minami, Yoritaka Sasaki, Yasuo Umezu, Masahiko Yamaguchi | ||||
| Palladium-catalyzed asymmetric allylic alkylation with an enamine as the nucleophilic reagent Tetrahedron Letters, Volume 48, Issue 43, 22 October 2007, Pages 7591-7594 Delong Liu, Fang Xie, Wanbin Zhang | ||||
| Novel ferrocenylphosphine-imines containing a pyridine unit as a new family of chiral ligands: the important influence of the position of the pyridine N-atom on the reactivity and enantioselectivity in palladium-catalyzed asymmetric allylic alkylations Tetrahedron: Asymmetry, Volume 15, Issue 7, 5 April 2004, Pages 1065-1068 Xiangping Hu, Huicong Dai, Changmin Bai, Huilin Chen, Zhuo Zheng | ||||
C30H27FeN2P
| Synthesis and use in palladium-catalyzed asymmetric allylic alkylation of new planar chiral chromium complexes of 1,2-disubstituted arenes having pyridine and aryl phosphine groups Tetrahedron: Asymmetry, Volume 10, Issue 15, 30 July 1999, Pages 2853-2861 Jin Wook Han, Hye-Young Jang, Young Keun Chung | ||||
| Enamines: efficient nucleophiles for the palladium-catalyzed asymmetric allylic alkylation Tetrahedron, Volume 65, Issue 2, 10 January 2009, Pages 512-517 Xiaohu Zhao, Delong Liu, Fang Xie, Wanbin Zhang | ||||
| New homochiral phosphine ligands having a hexahydro-1H-pyrrolo[1,2-c]imidazolone backbone: preparation and use for palladium-catalyzed asymmetric alkylation of cycloalkenyl carbonates Tetrahedron: Asymmetry, Volume 13, Issue 16, 27 August 2002, Pages 1769-1772 Kazutaka Shibatomi, Yasuhiro Uozumi | ||||
C30H27N2OP E.e. >99% [α]D19=+44 (c 1.4, chloroform) Source of chirality: -proline
(3R,7aS)-(3-(2-Diphenylphosphino)phenyl-6-hydroxy-2-phenyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one
C30H27N2OP E.e. >99% [α]D19=+9 (c 1.6, chloroform) Source of chirality: trans-4-hydroxy--proline
(3S,9aS)-(3-(2-Diphenylphosphino)phenyl-2-phenyl)tetrahydro-1H-imidazo[1,5-a]indole-1-one
C34H27N2OP E.e. >99% [α]D25=+135 (c 1.0, chloroform) Source of chirality: (S)-indoline-2-carboxylic acid
(3S,9aS)-(3-(2-Diphenylphosphino)phenyl-2-phenyl)tetrahydro-1H-imidazo[1,5-a]indole-1-one
C34H27N2OP E.e. >99% [α]D19=+127 (c 0.7, chloroform) Source of chirality: (S)-indoline-2-carboxylic acid
(3R,10aS)-(3-(2-Diphenylphosphino)phenyl-2-phenyl)tetrahydro-1H,5H-imidazo[1,5-b]isoquinoline-1-one
C35H29N2OP E.e. >99% [α]D25=+6 (c 0.5, chloroform) Source of chirality: (S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
| Palladium-catalyzed asymmetric allylic alkylation using chiral hydrazone ligands with ferrocene skeleton Journal of Organometallic Chemistry, Volume 689, Issue 17, 1 September 2004, Pages 2833-2836 Takashi Mino, Hiroshi Segawa, Masakazu Yamashita | ||||
| Asymmetric allylic alkylation catalyzed by palladium complexes with atropisomeric quinazolinone phosphine ligands Tetrahedron Letters, Volume 40, Issue 7, 12 February 1999, Pages 1245-1248 Xuedong Dai, Scott Virgil | ||||
| Asymmetric allylic alkylation catalyzed by palladium complexes with a new chiral bisphosphine ligand Tetrahedron Letters, Volume 38, Issue 3, 20 January 1997, Pages 375-378 James M. Longmire, Guoxin Zhu, Xumu Zhang | ||||
| Preparation of a new FerroPHOS derivative for palladium-catalyzed asymmetric allylic alkylations Tetrahedron: Asymmetry, Volume 12, Issue 1, 5 February 2001, Pages 33-35 Jahyo Kang, Jun Hee Lee, Jung Sun Choi | ||||
C42H44FeO2P2 [α]D29 −9.33 (c 0.54, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: (pS,pS)
(−)-(S)-Dimethyl (1,3-diphenylprop-2-en-1-yl)malonate
C20H20O4 Ee=96.3% [α]D27=−19.6 (c 1.4, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: (S)
| New chiral phosphinooxathiane ligands for palladium-catalyzed asymmetric allylic substitution reactions Tetrahedron Letters, Volume 41, Issue 23, 12 June 2000, Pages 4615-4618 Hiroto Nakano, Yuko Okuyama, Hiroshi Hongo* | ||||
| Chiral ferrocene-based phosphine-imine and sulfur-imine ligands for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl esters Journal of Molecular Catalysis A: Chemical, Volume 218, Issue 1, 17 August 2004, Pages 107-112 Xiangping Hu, Changmin Bai, Huicong Dai, Huilin Chen, Zhuo Zheng | ||||
| Asymmetric allylic alkylation of cycloalkenediol diacetates using a chiral phosphine ligand bearing a carboxyl group Tetrahedron: Asymmetry, Volume 11, Issue 6, 7 April 2000, Pages 1397-1403 Tatsuo Okauchi, Kouji Fujita, Tsuneyuki Ohtaguro, Satomi Ohshima, Toru Minami* | ||||
| Asymmetric allylic alkylation catalyzed by palladium complexes with new chiral ligands Tetrahedron Letters, Volume 37, Issue 26, 24 June 1996, Pages 4475-4478 Guoxin Zhu, Michael Terry, Xumu Zhang | ||||
| (−)-α-Isosparteine as a chiral ligand in asymmetric allylic alkylation Tetrahedron: Asymmetry, Volume 5, Issue 7, July 1994, Pages 1347-1352 Jahyo Kang, Won Oh Cho, Hyung^Geun Cho | ||||
Compound formula E.e = 88% [α]D22 = +11.98 (c = 0.69, EtOH) Source of chirality: asymm. syn. Absolute configuration: R
Methyl (R)-carbomethoxy-3-methylhex-4-enoate
Compound formula E.e = 60% [α]D22 = +15.43 (c = 0.92, CHCl3) Source of chirality: asymm. syn. Absolute configuration: R
Dimethyl (S)-2-cyclohexen-1-ylmalonate
Compound formula E.e = 62% [α]D22 = −8.69 (c = 1.36, CH2Cl2) Source of chirality: asymm. syn. Absolute configuration: S
| β-Hydroxy and β-(o-diphosphino)benzoyloxy(o-diphosphino) benzamides as ligands for asymmetric allylic alkylation Tetrahedron: Asymmetry, Volume 20, Issue 10, 5 June 2009, Pages 1132-1137 Geetanjali S. Mahadik, Stanley A. Knott, Lisa F. Szczepura, Shawn R. Hitchcock | ||||
C28H25NO2P Source of chirality: (1R,2S)-norephedrine Absolute configuration: (1R,2S) (c 0.10, CHCl3)
2-(Diphenylphosphino)-N-(1S,2S)-1-hydroxy-1-hydroxy-1-phenyl-2-propyl)benzamide
C28H25NO2P Source of chirality: (1S,2S)-pseudo norephedrine Absolute configuration: (1S,2S) (c 0.10, CHCl3)
(1R,2S)-2-(2-Diphenylphosphino)benzamido)-1-phenylpropyl 2-(diphenylphosphino)benzoate
C47H39NO3P2 Source of chirality: (1R,2S)-norephedrine Absolute configuration: (1R,2S) (c 0.10, CHCl3)
(1S,2S)-2-(2-Diphenylphosphino)benzamido)-1-phenylpropyl 2-(diphenylphosphino)benzoate
C47H39NO3P2 Source of chirality: (1S,2S)-pseudonorephedrine Absolute configuration: (1S,2S) (c 0.10, CHCl3)
| Readily available phosphine–imine ligands from α-phenylethylamine for highly efficient Pd-catalyzed asymmetric allylic alkylation Journal of Molecular Catalysis A: Chemical, Volume 270, Issues 1-2, 1 June 2007, Pages 127-131 Jia-Di Huang, Xiang-Ping Hu, Sai-Bo Yu, Jun Deng, Dao-Yong Wang, Zheng-Chao Duan, Zhuo Zheng | ||||
| Microwave-mediated palladium-catalyzed asymmetric allylic alkylation; an example of highly selective fast chemistry Journal of Organometallic Chemistry, Volume 603, Issue 1, 22 May 2000, Pages 2-5 Nils-Fredrik K. Kaiser, Ulf Bremberg, Mats Larhed, Christina Moberg*, Anders Hallberg* | ||||
| Reversal in enantioselectivity for the palladium-catalyzed asymmetric allylic substitution with novel metallocene-based planar chiral diphosphine ligands Tetrahedron Letters, Volume 49, Issue 6, 4 February 2008, Pages 1012-1015 Fang Xie, Delong Liu, Wanbin Zhang | ||||
| New chiral phosphinooxazolidine ligands for palladium-catalyzed asymmetric allylic substitution Tetrahedron Letters, Volume 40, Issue 28, 9 July 1999, Pages 5197-5198 Myung-Jong Jin, Jung-Ae Jung, Sang-Han Kim | ||||
| New chiral phosphinoimidazolidine ligand in palladium-catalyzed asymmetric allylic substitution Tetrahedron Letters, Volume 43, Issue 41, 7 October 2002, Pages 7409-7411 Myung-Jong Jin, Sang-Han Kim, Sang-Joon Lee, Young-Mok Kim | ||||
| Palladium-catalyzed asymmetric intramolecular allylation forming optically active vinylcyclopropane and vinyldihydrofurans Tetrahedron Letters, Volume 29, Issue 6, 1988, Pages 669-672 Tamio Hayashi, Akihiro Yamamoto, Yoshihiko Ito | ||||
| Simple Tetrahedron Letters, Volume 49, Issue 47, 17 November 2008, Pages 6635-6638 Katarzyna Glegoła, Sine A. Johannesen, Laura Thim, Catherine Goux-Henry, Troels Skrydstrup, Eric Framery | ||||
| C–C Bond Formation (Part 2) by Substitution Reactions: Allylic Alkylation Comprehensive Organometallic Chemistry III, 2007, Chapter 11.03, Pages 75-122 Y. Nishibayashi, S. Uemura | ||||
| Palladium-catalyzed allylic alkylation of tert-butyl(diphenylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions Tetrahedron: Asymmetry, Volume 12, Issue 11, 4 July 2001, Pages 1567-1571 Guoshu Chen, Yijian Deng, Liuzhu Gong, Aiqiao Mi, Xin Cui, Yaozhong Jiang, Michael C. K. Choi, Albert S. C. Chan | ||||
| Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 48, Issue 10, 5 March 2007, Pages 1703-1706 Biao Jiang, Zuo-Gang Huang | ||||
| Total synthesis of rac-longamide B Tetrahedron Letters, Volume 48, Issue 19, 7 May 2007, Pages 3459-3461 Xue-Tong Sun, Austin Chen | ||||
| Palladium-catalyzed asymmetric allylic substitution with a cyclopentadienide: asymmetric synthesis of metallocenes Tetrahedron: Asymmetry, Volume 14, Issue 4, 21 February 2003, Pages 511-515 Toshimasa Suzuka, Motoi Kawatsura, Atsushi Okada, Tamio Hayashi | ||||
C40H34Fe E.e. >99% (by preparation method) [α]D20=−249 (c 1.0, CHCl3) Source of chirality: chiral catalyst Absolute configuration: R,R
1,1′-Bis((R)-1,3-diphenyl-2-propenyl)zirconocene dichloride
C40H34Cl2Zr E.e. >99% (by preparation method) [α]D20=−119 (c 1.0, CHCl3) Source of chirality: chiral catalyst Absolute configuration: R,R
1,1′-Bis((R)-1,3-diphenyl-2-propenyl)titanocene dichloride
C40H34Cl2Ti E.e. >99% (by preparation method) [α]D20=+133 (c 1.0, CHCl3) Source of chirality: chiral catalyst Absolute configuration: R,R
| Development of chiral phosphine ligands bearing a carboxyl group and their application to catalytic asymmetric reaction Tetrahedron: Asymmetry, Volume 6, Issue 10, October 1995, Pages 2469-2474 Toru Minami, Yoshiharu Okada, Tsuneyuki Otaguro, Seiji Tawaraya, Tomohiro Furuichi, Tatsuo Okauchi | ||||
| Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (−)-paroxetine Tetrahedron Letters, Volume 48, Issue 29, 16 July 2007, Pages 4977-4981 Tetsuhiro Nemoto, Tatsurou Sakamoto, Takashi Fukuyama, Yasumasa Hamada | ||||
| P-stereogenic P/N hybrid ligands: a remarkable switch in enantioselectivity in palladium-catalyzed asymmetric allylation Tetrahedron Letters, Volume 45, Issue 3, 12 January 2004, Pages 603-606 Hiroshi Danjo, Masato Higuchi, Mitsuhiro Yada, Tsuneo Imamoto | ||||
| Novel chiral P,O-ligands for homogeneous Pd(0) catalysed asymmetric allylic alkylation reactions Tetrahedron: Asymmetry, Volume 19, Issue 4, 4 March 2008, Pages 454-458 Vanda Raquel Marinho, Ana Isabel Rodrigues, Anthony J. Burke | ||||
C27H24NO2P Source of chirality: (S)-phenylglycine Absolute configuration: (S) (c 0.41, CHCl3)
(S)-N-(1-Benzyl-2-hydroxyethyl)-2-(diphenylphosphino)benzamide 5b
C28H26NO2P Source of chirality: (S)-phenylalanine Absolute configuration: (S) (c 0.55, CHCl3)
| Thioether containing ligands for asymmetric allylic substitution reactions Comptes Rendus Chimie, Volume 10, Issue 3, March 2007, Pages 188-205 Erika Martin, Montserrat Diéguez | ||||
| A third generation chiral phosphorus-containing dendrimer as ligand in Pd-catalyzed asymmetric allylic alkylation Tetrahedron Letters, Volume 46, Issue 38, 19 September 2005, Pages 6503-6506 Régis Laurent, Anne-Marie Caminade, Jean-Pierre Majoral | ||||
| Preparation of α-substituted allylboronates by chemoselective iridium-catalyzed asymmetric allylic alkylation of 1-propenylboronates Tetrahedron Letters, Volume 48, Issue 18, 30 April 2007, Pages 3305-3309 Feng Peng, Dennis G. Hall | ||||
| Palladium-catalyzed asymmetric alkylation via π-allyl intermediate: Acetamidomalonate ester as a nucleophile. Tetrahedron Letters, Volume 31, Issue 35, 1990, Pages 5049-5052 Motowo Yamaguchi, Toshihide Shima, Takamichi Yamagishi, Mitsuhiko Hida | ||||
| Chiral sulfoxide ligands bearing nitrogen atoms as stereocontrollable coordinating elements in palladium-catalyzed asymmetric allylic alkylations Tetrahedron: Asymmetry, Volume 9, Issue 21, 6 November 1998, Pages 3797-3817 Kunio Hiroi, Yoshio Suzuki, Ikuko Abe, Yutaka Hasegawa, Kenji Suzuki | ||||
| New chiral o-(phosphinoamido)phenyl sulfoxide ligands in palladium-catalyzed asymmetric allylic alkylations Tetrahedron Letters, Volume 39, Issue 36, 3 September 1998, Pages 6499-6502 Kunio Hiroi, Yoshio Suzuki | ||||
| Palladium-catalyzed asymmetric telomerization of isoprene. Preparation of optically active citronellol Journal of Organometallic Chemistry, Volume 232, Issue 1, 8 June 1982, Pages 89-98 Masanobu Hidai, Haruyoshi Mizuta, Hiroshi Yagi, Yozo Nagai, Kenji Hata, Yasuzo Uchida | ||||
| Asymmetric allylic alkylation catalyzed by palladium-sparteine complexes Tetrahedron: Asymmetry, Volume 2, Issue 7, 1991, Pages 683-690 Antonio Togni | ||||
C18H31F6N2PPd E.e.=100 % [α]22D=−67 (c=1.035, CH2Cl2) Source of chirality: natural Absolute configuration (of natural (−)-sparteine): 6R,7S,9S,11S
| Pd-catalyzed asymmetric allylic alkylation with nitromethane using a chiral diaminophosphine oxide: (S,RP)-Ph-DIAPHOX. Enantioselective synthesis of (R)-preclamol and (R)-baclofen Tetrahedron Letters, Volume 47, Issue 37, 11 September 2006, Pages 6577-6581 Tetsuhiro Nemoto, Long Jin, Hiroshi Nakamura, Yasumasa Hamada | ||||
| New chiral phosphine–amide ligands in palladium-catalysed asymmetric allylic alkylations Tetrahedron: Asymmetry, Volume 12, Issue 2, 19 February 2001, Pages 287-291 Takashi Mino, Kohki Kashihara, Masakazu Yamashita | ||||
C29H28NO2P Ee=>95% [α]D20=−14.5 (c 0.80, CHCl3) Source of chirality: (S)-(+)-2-amino-1-methoxy-3-phenylpropane Absolute configuration: S
(S)-N-(1-Benzyl-2-methoxyethyl)-2-hydroxynaphthalenecarboxamide
C21H21NO3 Ee=>95% [α]D25=−54.4 (c 0.16, CHCl3) Source of chirality: (S)-(+)-2-amino-1-methoxy-3-phenylpropane Absolute configuration: S
(S)-N-(1-Benzyl-2-methoxyethyl)-2-(trifluoromethanesulfonyloxy)naphthalenecarboxamide
C22H20F3NO5S Ee=>95% [α]D25=−23.7 (c 0.35, CHCl3) Source of chirality: (S)-(+)-2-amino-1-methoxy-3-phenylpropane Absolute configuration: S
(S)-N-(1-Benzyl-2-methoxyethyl)-2-(diphenylphosphino)naphthalenecarboxamide
C33H30NO2P Ee=>95% [α]D25=−18.7 (c 0.17, CHCl3) Source of chirality: (S)-(+)-2-amino-1-methoxy-3-phenylpropane Absolute configuration: S
| Application of phosphinous amide ligands in palladium complex-catalyzed asymmetric allylic alkylation: influence of steric effects on enantioselectivity Tetrahedron: Asymmetry, Volume 15, Issue 2, 26 January 2004, Pages 213-217 Xuanhua Chen, Rongwei Guo, Yueming Li, Gang Chen, Chi-Hung Yeung, Albert S. C. Chan | ||||
C52H58N2P2Absolute configuration: (R)[α]20D=+3.3 (c 1.0, THF)Source of chirality: (R)-H8-BINAM
| Enantioselective palladium catalyzed allylic alkylation with phosphorus-containing C2-symmetric chiral amine ligands Tetrahedron Letters, Volume 35, Issue 36, 5 September 1994, Pages 6689-6692 Hideki Kubota, Kenji Koga | ||||
| Asymmetric allylic alkylation using a polymer-supported palladium catalyst in the presence of chiral ligands Journal of Molecular Catalysis A: Chemical, Volume 201, Issues 1-2, 1 July 2003, Pages 131-135 Maria Michela Dell’Anna, Piero Mastrorilli, Cosimo Francesco Nobile, Gian Paolo Suranna | ||||
| Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane Tetrahedron: Asymmetry, Volume 9, Issue 3, 13 February 1998, Pages 397-401 Waldemar Adam, Rainer T. Fell, Chantu R. Saha-Möller, Cong-Gui Zhao | ||||
| Synthesis of optically active α-sulfinylacetaldehyde Tetrahedron Letters, Volume 29, Issue 51, 1988, Pages 6775-6778 P. Pflieger, C. Mioskowski, J. P. Salaun, D. Weissbart, F. Durst | ||||
| Optically active pyrazolylborate: synthesis, characterization and uses in enantioselective cyclopropanation reaction Journal of Molecular Catalysis A: Chemical, Volume 185, Issues 1-2, 8 July 2002, Pages 33-39 Udai P. Singh, Preeti Babbar, Bernd Hassler, H. Nishiyama, H. Brunner | ||||
| New chiral ligands, pyrrolidinyl- and 2-azanorbornyl- phosphinooxazolidines for palladium-catalyzed asymmetric allylation Tetrahedron: Asymmetry, Volume 11, Issue 5, 24 March 2000, Pages 1193-1198 Yuko Okuyama, Hiroto Nakano, Hiroshi Hongo * | ||||
| Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide Tetrahedron Letters, Volume 48, Issue 36, 3 September 2007, Pages 6304-6307 Tetsuhiro Nemoto, Teisuke Harada, Takayoshi Matsumoto, Yasumasa Hamada | ||||
| Pd-catalyzed asymmetric allylic alkylation using furanoside diphosphinite ligands Inorganica Chimica Acta, Volume 358, Issue 13, 1 September 2005, Pages 3824-3828 Eugeni Guimet, Montserrat Diéguez, Aurora Ruiz, Carmen Claver | ||||
| The use of a new carboranylamidophosphite ligand in the asymmetric Pd-catalysed allylic alkylation in organic solvents and supercritical carbon dioxide Journal of Organometallic Chemistry, Volume 694, Issue 19, 1 September 2009, Pages 3047-3049 Sergey E. Lyubimov, Ilya V. Kuchurov, Andrei A. Vasil’ev, Andrey A. Tyutyunov, Valery N. Kalinin, Vadim A. Davankov, Sergei G. Zlotin | ||||
| Palladium-catalyzed allylic alkylation of optically active α-alkenyl-α-acyloxytrialkylsilane Tetrahedron Letters, Volume 46, Issue 30, 25 July 2005, Pages 5009-5012 Kazuhiko Sakaguchi, Takeshi Yamada, Yasufumi Ohfune | ||||
| Kinetic resolution of allylic esters in palladium-catalyzed asymmetric allylic alkylations using C–N bond axially chiral aminophosphine ligands Tetrahedron: Asymmetry, Volume 19, Issue 23, 1 December 2008, Pages 2711-2716 Takashi Mino, Kazuya Wakui, Shunsuke Oishi, Youtaro Hattori, Masami Sakamoto, Tsutomu Fujita | ||||
C17H16O2 Ee = 95% (chiral HPLC) Source of chirality: asymmetric synthesis Absolute configuration: (R) (c 0.30, CHCl3)
(R)-1,3-Diphenylprop-2-en-1-yl pivalate
C20H22O2 Ee = 55% (chiral HPLC) Source of chirality: asymmetric synthesis Absolute configuration: (R) (c 0.35, CHCl3)
(R)-1,3-Diphenylprop-2-en-1-yl benzoate
C22H18O2 Ee = 59% (chiral HPLC) Source of chirality: asymmetric synthesis Absolute configuration: (R) (c 0.30, CHCl3)
| New monodentate chiral phosphine 2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1]nonane(9-PBN): Application to asymmetric allylic substitution reaction Tetrahedron Letters, Volume 37, Issue 42, 14 October 1996, Pages 7565-7568 Yasumasa Hamada, Noriko Seto, Hiroki Ohmori, Keiichiro Hatano | ||||
| Chiral, bicyclic proline derivatives and their application as ligands for copper in the catalytic asymmetric allylic oxidation of olefins Tetrahedron Letters, Volume 37, Issue 42, 14 October 1996, Pages 7577-7580 Mikael J. Södergren, Pher G. Andersson | ||||
| Asymmetric allylic oxidation of cycloalkenes using a tridentate tris(oxazoline) ligand as a chiral auxiliary Tetrahedron Letters, Volume 41, Issue 20, 21 May 2000, Pages 3941-3945 Yoshinori Kohmura, Tsutomu Katsuki | ||||
| Asymmetric allylic amination catalyzed by chiral ferrocenylphosphine-palladium complexes Tetrahedron Letters, Volume 31, Issue 12, 1990, Pages 1743-1746 Tamio Hayashi, Kohei Kishi, Akihiro Yamamoto and, Yoshihiko Ito | ||||
| Palladium-catalyzed asymmetric allylic alkylation using dimethyl malonate and its derivatives as nucleophile Tetrahedron: Asymmetry, Volume 2, Issue 7, 1991, Pages 663-666 Motowo Yamaguchi, Toshihide Shima, Takamichi Yamagishi, Mitsuhiko Hida | ||||
C22H23NO5 E.e. = 94% (by 1H NMR) [α]D20 =−51 (c = 0.6, EtOH) Circular dichroism: λEtOHmax (Δ Source of chirality: Asymm. synth. with palladium complex Absolute configuration: S (assigned by chemical transformation from dimethyl 2-((E)-1,3R-diphenyl-2-propenyl)malonate)
) = 288 nm (−0.18)
Dimethyl 2-((E)-1,3-diphenyl-2-propenyl)malonate
C20H20O4 E.e. = 90% (by 1H NMR) [α]D20 =+18 (c = 0.6, EtOH) Circular dichroism: λEtOHmax (Δ Source of chirality: Asymm. synth. with palladium complex Absolute configuration: R (ref. Hayashi, T.: Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.)) = 292 nm (−0.10)
Dimethyl 2-methyl-2-((E)-1,3-diphenyl-2-propenyl)malonate
C21H22O4 E.e. = 80% (by 1H NMR) [α]D20= −37 (c = 0.6, EtOH) Circular dichroism: λEtOHmax (Δ Source of chirality: Asymm. synth. with palladium complex Absolute configuration: R) = 295 nm (−0.15)
Dimethyl 2-trifluoroacetamido-2-((E)-1,3-diphenyl-2-propenyl)malonate
C22H20NO5F3 E.e. = 78% (by 1H NMR) [α]D20 =−41 (c = 0.6, EtOH) Circular dichroism: λEtOHmax (° Source of chirality: Asymm. synth. with palladium complex Absolute configuration: S) = 286nm (−0.43)
Dimethyl 2-methoxycarbonyl-2-((E)-1,3-diphenyl-2-propenyl)malonate
C22H22O6 E.e. = 81% (by 1H NMR) [α]D20 = −23 (c = 0.6, EtOH) Circular dichroism: λEtOHmax (Δ Source of chirality: Asymm. synth. with palladium complex Absolute configuration: S) = 290 nm (−0.36)
3-((E)-1,3-diphenyl-2-propenyl)-2,4-pentanedione
C20H20O2 E.e. = 90% (by 1H NMR) [α]D20 = −10(c = 0.6, EtOH) Source of chirality: Asymm. synth. with palladium complex Absolute configuration: R (ref. Hayashi, T.; Yamamoto, A.; Hagihara, T.; Ito, Y. Tetrahedron Lett. 1986, 27, 191.)
| Remote substituent effect in palladium/pyridinyl-oxazolines catalyzed asymmetric allylic alkylation Journal of Molecular Catalysis A: Chemical, Volume 193, Issues 1-2, 17 February 2003, Pages 89-95 Zhi-Peng Li, Fang-Yi Tang, Hua-Dong Xu, Xin-Yan Wu, Qi-Lin Zhou, Albert S. C. Chan | ||||
| New enantiopure cyclic β-iminophosphine ligands: applications in Pd-catalyzed asymmetric allylic substitution Tetrahedron Letters, Volume 44, Issue 11, 10 March 2003, Pages 2413-2415 Maria Zablocka, Marek Koprowski, Bruno Donnadieu, Jean-Pierre Majoral, Mathieu Achard, Gérard Buono | ||||
| Easily accessible ferrocenyl N-P/S type ligands and their applications in asymmetric allylic substitutions Tetrahedron: Asymmetry, Volume 17, Issue 4, 20 February 2006, Pages 497-499 Fuk Loi Lam, Terry T.L. Au-Yeung, Hong Yee Cheung, Stanton H.L. Kok, Wing Sze Lam, Kwok Yin Wong, Albert S.C. Chan | ||||
| Synthesis of novel chiral phosphine-triazine ligand derived from α-phenylethylamine for Pd-catalyzed asymmetric allylic alkylation Chinese Chemical Letters, Volume 19, Issue 3, March 2008, Pages 261-263 Jia Di Huang, Xiang Ping Hu, Zhuo Zheng | ||||
| Catalytic asymmetric synthesis of ethyl (1R,2S)-dehydrocoronamate Tetrahedron Letters, Volume 48, Issue 6, 5 February 2007, Pages 945-948 Martin E. Fox, Ian C. Lennon, Vittorio Farina | ||||
| New chiral chelating phosphine complexes containing tricarbonyl(η6-arene) chromium for highly enantioselective allylic alkylation Journal of Organometallic Chemistry, Volume 503, Issue 1, 1 November 1995, Pages 143-148 Yoshinori Hayashi, Hiroshi Sakai, Naotake Kaneta, Motokazu Uemura | ||||
| Furanoside thioether–phosphinite ligands for Pd-catalyzed asymmetric allylic substitution reactions: Scope and limitations Journal of Organometallic Chemistry, Volume 691, Issue 10, 1 May 2006, Pages 2257-2262 Montserrat Diéguez, Oscar Pàmies, Carmen Claver | ||||
| Synthesis of P-chirogenic diarylphosphinoacetic acids and their proline derivatives for palladium-catalysed allylic alkylation reactions Tetrahedron Letters, Volume 46, Issue 47, 21 November 2005, Pages 8145-8148 Hubert Lam, Peter N. Horton, Michael B. Hursthouse, David J. Aldous, King Kuok (Mimi) Hii | ||||
| The mechanism of enantioselective palladium(0)-catalyzed allylic alkylation with chiral oxazolinylpyridines: a DFT study Journal of Molecular Structure: THEOCHEM, Volume 716, Issues 1-3, 7 March 2005, Pages 79-87 Dianyong Tang, Xiaoling Luo, Wei Shen, Ming Li | ||||
| A new class of C2-symmetric diphosphine ligands derived from valine: remarkably diverse behavior in catalytic asymmetric transformations Tetrahedron: Asymmetry, Volume 10, Issue 23, 3 December 1999, Pages 4501-4511 Akihito Saitoh, Takashi Uda, Toshiaki Morimoto | ||||
| A convenient synthesis of optically active 1H-aziridine-2-carboxylic acids (esters) Tetrahedron Letters, Volume 30, Issue 36, 1989, Pages 4881-4884 J. Legters, L. Thijs, B. Zwanenburg | ||||
| Organogermanium compounds : XI. The stereochemistry of the reactions of optically active ethyl(1-naphthyl)phenylgermyllithium with some carbonyl compounds Journal of Organometallic Chemistry, Volume 37, Issue 2, 16 April 1972, Pages 267-274 C. Eaborn, R. E. E. Hill, P. Simpson | ||||
| A regiochemical control in the π-allylpalladium substitution. Preparation of optically active γ-silylallylamines Tetrahedron Letters, Volume 34, Issue 37, 10 September 1993, Pages 5919-5922 Hiroshi Inami, Takayori Ito, Hirokazu Urabe, Fumie Sato | ||||
| Synthetic approach to the total synthesis of fumitremorgins II synthesis of optically active pentacyclic intermediates and their dehydrogenation Tetrahedron Letters, Volume 27, Issue 28, 1986, Pages 3235-3238 Masako Nakagawa, Hiroshi Fukushima, Tomohiko Kawate, Mitsuya Hongu, Shin-ichi Kodato, Teruaki Une, Mikio Taniguchi, Tohru Hino | ||||
| The synthesis of optically active 2-phenylthio aldehydes Tetrahedron Letters, Volume 35, Issue 23, 6 June 1994, Pages 3991-3994 Kelly Chibale, Stuart Warren | ||||
| Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha Bioorganic & Medicinal Chemistry Letters, Volume 12, Issue 3, 11 February 2002, Pages 333-335 Hiroyuki Miyachi, Masahiro Nomura, Takahiro Tanase, Masahiro Suzuki, Koji Murakami, Katsuya Awano | ||||
| A new chiral host compound 10,10′-dihyrroxy-9,9′-biphenanthryl. Optical resolution of propionic acid derivatives, butyric acid derivatives, and 4-hydroxycyclopent-2-en-1-one derivatives by complexation Tetrahedron Letters, Volume 29, Issue 15, 1988, Pages 1807-1810 Fumio Toda, Koichi Tanaka | ||||
| Synthesis of new optically active cyanocyclopropanes as chiral dopants for ferroelectric liquid crystals Tetrahedron Letters, Volume 32, Issue 7, 11 February 1991, Pages 939-942 Tetsuo Kusumoto, Akiko Nakayama, Ken-ichi Sato, Tamejiro Hiyama, Sadao Takehara, Tadao Shoji, Masashi Osawa, Takeshi Kuriyama, Kayoko Nakamura, Toru Fujisawa | ||||
| Chirality recognition of 1,1′-bi-2-naphthol with optically active bis(oxazolinyl)pyridines Tetrahedron: Asymmetry, Volume 4, Issue 7, July 1993, Pages 1461-1464 Hisao Nishiyama, Tomonori Tajima, Masahiro Takayama, Kenji Itoh | ||||
C25H23N3O2 2,6-Bis[(S)-4′-benzyloxazolin-2′-yl]pyridine E.e. = 100 % [α]D22 =−71.7 (c 1.02, CH2Cl2) Source of chirality: natural Absolute configuration: 4′S,4″S (derived from L-phenylalanine)
| 2,2′-Bis(diarylstibano)-1,1′-binaphthyls (BINASbs); a useful chiral ligand for palladium-catalyzed asymmetric allylic alkylation, and the structure of a BINASb---PdCl2 complex Tetrahedron Letters, Volume 44, Issue 33, 11 August 2003, Pages 6217-6220 Shuji Yasuike, Satoru Okajima, Kentaro Yamaguchi, Jyoji Kurita | ||||
| Palladium-catalyzed asymmetric allylations of chiral enamines bearing phosphine functionality. Effects of anionic counterparts of allylating reagents on asymmetric induction Tetrahedron Letters, Volume 31, Issue 25, 1990, Pages 3623-3626 Kunio Hiroi, Jun Abe | ||||
| Palladium-catalyzed asymmetric alkylation of 2-azaallyl acetates for the synthesis of β-carboxyaspartic acid derivatives Journal of Molecular Catalysis A: Chemical, Volume 140, Issue 3, 23 April 1999, Pages 255-258 Motowo Yamaguchi, Kazue Ohba, Hiroyuki Tomonaga, Takamichi Yamagishi | ||||
| Preparation and application of polymer-supported π-allylpalladium complex as a chiral catalyst in the asymmetric allylic alkylation Journal of Molecular Catalysis A: Chemical, Volume 174, Issues 1-2, 1 October 2001, Pages 151-157 H. -J. Park, Jin Wook Han, Hwimin Seo, Hye-Young Jang, Young Keun Chung, Junghun Suh | ||||
| Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from Tetrahedron, Volume 63, Issue 30, 23 July 2007, Pages 7133-7141 Katarzyna Glegoła, Eric Framery, Catherine Goux-Henry, K. Michał Pietrusiewicz, Denis Sinou | ||||
| Palladium-catalyzed asymmetric allylic alkylation using iminophosphine ligands derived from chiral primary 1-ferrocenylalkylamines Tetrahedron: Asymmetry, Volume 12, Issue 20, 13 November 2001, Pages 2793-2799 Tsutomu Fukuda, Akihiro Takehara, Masatomo Iwao | ||||
C31H28FeNP [α]D26=+106 (c 1.01, CHCl3) Source of chirality: (S)-1-ferrocenylethylamine Absolute configuration: S
(S)-N-[2-(Diphenylphosphino)benzylidene]-1-ferrocenylpentylamine
C34H34FeNP [α]D26=+92.6 (c 1.04, CHCl3) Source of chirality: (S)-1-ferrocenylpentylamine Absolute configuration: S
(S)-N-[2-(Diphenylphosphino)benzylidene]-1-ferrocenyl-2,2-dimethylpropylamine
C34H34FeNP [α]D26=+72.2 (c 1.03, CHCl3) Source of chirality: (S)-1-ferrocenyl-2,2-dimethylpropylamine Absolute configuration: S
(S)-N-[2-(Diphenylphosphino)benzylidene]-α-ferrocenylbenzylamine
C36H30FeNP [α]D27=+107 (c 1.04, CHCl3) Source of chirality: (S)-α-ferrocenylbenzylamine Absolute configuration: S
| SYNTHESES OF OPTICALLY ACTIVE (+)- AND (−)-UNTENONE A Tetrahedron, Volume 51, Issue 32, 7 August 1995, Pages 8749-8756 Hiroaki Miyaoka, Tatsuhiko Watanuki, Yasuhiro Saka, Yasuji Yamada | ||||
| The synthesis of novel C2-symmetric P,N-chelation ruthenocene ligands and their application in palladium-catalyzed asymmetric allylic substitution Tetrahedron Letters, Volume 48, Issue 4, 22 January 2007, Pages 585-588 Delong Liu, Fang Xie, Wanbin Zhang | ||||
| The preparation of optically active 3-fluoro-β-lactam derivatives Journal of Fluorine Chemistry, Volume 54, Issues 1-3, September-October 1991, Page 193 J. T. Welch, R. Kawecki, J. A. Wichtowski, K. Araki | ||||
| Microbiological synthesis and circular dichroism of optically active 2-deuterio-cycloalkanones Tetrahedron Letters, Volume 21, Issue 44, 1980, Pages 4275-4278 G. Dauphin, J. C. Cramain, A. Kergomard, M. F. Renard, H. Veschambre | ||||
| Convergent synthesis of optically active bifunctionalized [7]thiaheterohelicene Tetrahedron Letters, Volume 36, Issue 6, 6 February 1995, Pages 915-918 Kazuhiko Tanaka, Hideji Osuga, Yuka Shogase, Hitomi Suzuki | ||||
| Optically active tricarbonyl(cyclohexadienyl)iron(1+) salts: Synthetic equivalents to spatially directed organic cations Tetrahedron Letters, Volume 22, Issue 8, 1981, Pages 779-782 Arthur J. Birch, G. Richard Stephenson | ||||
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