Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry

Zaed, A. M., Grafton, M. W., Ahmad, S. and Sutherland, A. (2014) Asymmetric synthesis of cis-aminocyclopentenols, building blocks for medicinal chemistry. Journal of Organic Chemistry, 79(3), pp. 1511-1515. (doi: 10.1021/jo402712r)

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Abstract

A highly efficient one-pot multistep process involving an asymmetric Pd(II)-catalyzed Overman rearrangement and a Ru(II)-catalyzed ring-closing metathesis reaction has been developed for the preparation of (R)- or (S)-aminocyclopenta-2-enes. The rapid strategy employed and the relatively mild conditions of the one-pot process allowed the multigram synthesis of the carbocycles in high enantiomeric excess (92% ee). The synthetic utility of these compounds was demonstrated by the stereoselective incorporation of hydroxyl groups, generating cis-4- and cis-5-aminocyclopenta-2-en-1-ols, important building blocks for medicinal chemistry.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Grafton, Mr Mark and Zaed, Mr Ahmed Mohamed and Ahmad, Mr Sajjad and Sutherland, Professor Andrew
Authors: Zaed, A. M., Grafton, M. W., Ahmad, S., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904

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