ScienceDirect - Tetrahedron Letters : Lithium diphenylcuprate reactions with 4-tosyloxy-L-prolines; an interesting stereochemical outcome : : A synthesis of TRANS-4-phenyl-L-proline.

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 151-154

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Stereocontrol in reactions of cyclic and acyclic [beta]...
Comptes Rendus Chimie

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Stereocontrol in reactions of cyclic and acyclic β-silyl radicals
Comptes Rendus Chimie, Volume 8, Issue 5, May 2005, Pages 823-832
Yannick Landais

Abstract

1,2-Stereocontrol in reactions of chiral β-silylcarboradicals is discussed, with examples of stereoinduction arising from bromination, selenenylation, azidation, and 5-exo-trig cyclizations. Transition state models, based on A_1,3 interactions and torsional strain have been proposed which allow for reliable predictions of the stereochemical course of these processes. These models parallel those developed earlier in ionic (electrophilic and nucleophilic) processes. To cite this article: Y. Landais, C. R. Chimie 8 (2005).

Résumé

Le stéréocontrôle-1,2 dans les réactions des radicaux carbonés β-silylés chiraux est discuté à l'aide de quelques exemples de stéréoinduction observés lors des processus de bromation, sélénénylation, azidation et de cyclisation 5-exo-trig. Des modèles d'états de transition, fondés sur la contrainte allylique et sur les contraintes de torsion sont proposés et permettent de prédire le cours stéréochimique de ces processus. Ces modèles sont très proches de ceux développés précédemment pour les processus ioniques (électrophiles et nucléophiles). Pour citer cet article: Y. Landais, C. R. Chimie 8 (2005).

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doi:10.1016/S0040-4039(00)83964-7

Lithium diphenylcuprate reactions with 4-tosyloxy-L-prolines; an interesting stereochemical outcome : A synthesis of TRANS-4-phenyl-L-proline.

John K. Thottathil and Jerome L. Moniot

Squibb Chemical Division, P. O. Box 4000, Princeton, N. J. 08540 U.S.A.

Received 20 September 1985.

Available online 8 March 2001.

Abstract

The reaction of lithium diphenylcuprate with trans-4- and cis-4-tosyloxy-L-prolines gives excellent yields of 4-phenyl substituted L-prolines and the reaction proceeds with net retention of configuration at the carbon center bearing the tosyloxy group.

References

E.W. Petrillo, Jr. and M.A. Ondetti Med. Res. Rev. 2 (1982), p. 1. Full Text via CrossRef
b. E. W. Petrillo, Jr., Eur. Pat. EP 063896 (1982).
c. E. W. Petrillo, Jr., Eur. Pat. EP 053902 (1982).

Prepared as shown below:

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P.G.M. Wuts Synthetic Comm. 11 (1981), p. 139. Full Text via CrossRef
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C.R. Johnson and G. Dutra J. Am. Chem. Soc. 95 (1973), p. 7783. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (22)
G.H. Posner Org. React. 22 (1975), p. 253.

Dr. E.W. Petrillo, Jr., of the Squibb Institute for Medical Research, has proven the structure and stereochemistry of compound . obtained by an independent method by single crystal X-ray analysis an we thank Dr. Petrillo for this information.

H.H. Wasserman, W.T. Han, J.M. Schaus and J.W. Faller Tetrahedron Lett. 25 (1984), p. 3111. Abstract | PDF (215 K) | View Record in Scopus | Cited By in Scopus (2)

We thank Professor Wasserman for bringing this article to our attention and for the cordial discussion we had on this topic.

M. Nakajima, A. Torikata, H. Tamaoki, T. Haneishi, M. Arai, T. Kinoshita and H. Kuwano J. Antibiotics 36 (1983), p. 967. View Record in Scopus | Cited By in Scopus (2)
K. Fukushima, T. Arai, Y. Mori, M. Tsuboi and M. Suzuki J. Antibiotics 26 (1983), p. 1612.
R.D. Birkenmeyer and F. Kagan J. Med. Chem. 13 (1970), p. 616. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (12)

Detailed studies of these reactions including mechanistic aspects, reaction with other substrates, reactions using other dialkylorganocuprates and other organoheterocuprates and the various analytical methods used to determine the absolute configuration of each of the four 4-phenyl proline isomers will be published elsewhere.

Dr. D. M. Floyd.The Squibb Institute for Medical Research, Unpublished results.

Satisfactory IR, NMR (¹H, ¹³C), and/or elemental analysis were obtained for all new compounds.

Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 151-154

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