Issue 18, 2000

Asymmetric reduction of prochiral cycloalkenones. The influence of exocyclic alkene geometry

Abstract

The asymmetric reduction of a series of prochiral enones of general structure 1 using the Corey oxazaborolidine 2, leading to enantiomerically enriched allylic cycloalkanols 3 is described. The influence of alkene geometry on both the sense (Rvs. S ) and efficiency (% ee) of the asymmetric reduction process has been probed for two systems, (E )- and (Z )-4 and (E )- and (Z )-7, based on cyclohexanone and cyclopentanone respectively. The absolute stereochemistry of the cyclopentyl derivative (E )-8 has been established by X-ray crystallographic analysis of carbamate 10. The ability to assign an absolute configuration to allylic alcohols 3, based on the NMR methods described earlier by Riguera, has been evaluated.

Supplementary files

Article information

Article type
Paper
Submitted
07 Jun 2000
Accepted
20 Jul 2000
First published
23 Aug 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3047-3054

Asymmetric reduction of prochiral cycloalkenones. The influence of exocyclic alkene geometry

A. F. Simpson, C. D. Bodkin, C. P. Butts, M. A. Armitage and T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 2000, 3047 DOI: 10.1039/B004540N

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