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7444073 
Journal Article 
Asymmetric reduction of prochiral cycloalkenones. The influence of exocyclic alkene geometry 
Simpson, AF; Bodkin, CD; Butts, CP; Armitage, MA; Gallagher, T 
2000 
Journal of the Chemical Society, Perkin Transactions 1
ISSN: 1472-7781
EISSN: 1364-5463 
ROYAL SOC CHEMISTRY 
CAMBRIDGE 
18 
3047-3054 
English 
WOS:000089170300009 
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 (R vs. 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. 
Alcohols; Derivatives; Molecular structure; Nuclear magnetic resonance; Olefins; Reduction; Stereochemistry; X ray crystallography; Asymmetric reduction; Aromatic hydrocarbons 
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