ScienceDirect - Tetrahedron Letters : Modification of optically active ferrocenylphosphine ligands for palladium-catalyzed asymmetric allylic alkylation

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 191-194

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doi:10.1016/S0040-4039(00)83974-X

Modification of optically active ferrocenylphosphine ligands for palladium-catalyzed asymmetric allylic alkylation

Tamio Hayashi, ^*, Akihiro Yamamoto, Toshiya Hagihara and Yoshihiko Ito

Department of Synthetic Chemistry, Kyoto University, Kyoto 606, Japan

Received 28 September 1985.

Available online8 March 2001.

Abstract

Optically active ferrocenylphosphines containing a functional group on the side chain were effective as ligands for the palladium—catalyzed asymmetric allylic alkylation of 1,3-disubstituted allyl acetates such as l,3-diphenyl-3-acetoxy-l-propene with sodium acetylacetonate and related soft carbon nucleophiles to give the alkylation products of up to 92% ee.

References

For reviews H.B. Kagan and J.C. Fiaud Top. Stereochem 10 (1978), p. 175.
B. Bosnich and M.D. Fryzuk Top. Stereochem. 12 (1981), p. 119. Full Text via CrossRef
T. Hayashi and M. Kumada In: J.D. Morrison, Editor, Asymmetric Synthesis 5, Academic Press, Inc., New York (1985) Chap. 5 .

T. Hayashi and M. Kumada Acc. Chem. Res. 15 (1982), p. 395. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (98)

First example of this type of asymmetric ally lie alkylation has been reported by Trost: B.M. Trost and P.E. Strege J. Am. Chem. Soc. 99 (1977), p. 1649. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (58)
Very recently, Trost has reported the asymmetric synthesis of 69% ee: B.M. Trost and D.J. Murphy Organometallics 4 (1985), p. 1143. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (225)

For other types of palladium-catalyzed asymmetric allylation: P.R. Auburn, P.B. Mackenzie and B. Bosnich J. Am. Chem. Soc. 107 (1985), p. 2033. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (239)
K. Yamamoto and J. Tsuji Tetrahedron Lett. 23 (1982), p. 3089. Abstract | PDF (219 K) | View Record in Scopus | Cited By in Scopus (16)
J.C. Fiaud, A. Hibon de Gournay, M. Larcheveque and H.B. Kagan J. Organomet. Chem. 154 (1978), p. 175. Abstract | PDF (837 K) | View Record in Scopus | Cited By in Scopus (30)
T. Hayashi, K. Kanehira, H. Tsuchiya and M. Kumada J. Chem. Soc. (1982), p. 1162 Chem. Commun. . Full Text via CrossRef

For asymmetric allylation of Grignard reagents catalyzed by nickel complexes: G. Consiglio, F. Morandini and O. Piccolo J. Chem. Soc. 112 (1983) Chem. Commun. .
T. Hiyama and N. Wakasa Tetrahedron Lett. 26 (1985), p. 3259. Abstract | PDF (259 K) | View Record in Scopus | Cited By in Scopus (24)

B.M. Trost, L. Weber, P.E. Strege, T.J. Fullerton and T.J. Dietsche J. Am. Chem. Soc. 100 (198), p. 3416.

B.M. Trost Acc. Chem. Res. 13 (1980), p. 385. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (240)

T. Hayashi, M. Konishi and M. Kumada J. Chem. Soc. (1983), p. 736 Chem. Commun. . Full Text via CrossRef
T. Hayashi, T. Hagihara, M. Konishi and M. Kumada J. Am. Chem. Soc. 105 (1983), p. 7767. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (58)
T. Hayashi, M. Konishi and M. Kumada J. Chem. Soc. 107 (1984) Chem. Commun. .

T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi, K. Yamamoto and M. Kumada Bull. Chem. Soe. Jpn. 53 (1980), p. 1138. Full Text via CrossRef

H.B. Kagan and T.P. Dang J. Am. Chem. Soc. 94 (1972), p. 6429. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (321)

K. Achiwa J. Am. Chem. Soc. 98 (1976), p. 8265. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (66)

The following transformations were carried out:

Full-size image

a) NaOMe/MeOH, reflux b) NaCN/LiI/DMF, 120° c) 1. Cp₂TiCH₂ClAlMe₂/THF 2. aq.HCl/THF d) 1. KMnO₄/NaIO₄ 2. CH₂/THF

H. Wren and H. Williams J. Chem. Soc. 109 (1916), p. 572. Full Text via CrossRef

G.R. Sullivan Top. Stereochem. 10 (1978), p. 287.
R.E. Eraser In: J.D. Morrison, Editor, Asymmetaric Synthesis 1, Academic Press, Inc., New York (1983) Chap. 9 .

Enantiomeric purity was determined by ¹H NMR of ( , )-(+)-9^3a using Eu(dcm)3.¹³

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 191-194

Result list | previous < 18 of 36 > next

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