Asymmetric wittig reaction of chiral arsonium ylides—I. Asymmetric olefination of 4-substituted cyclohexanones

Abstract

Asymmetric Wittig-type olefination of 4-substituted cyclohexanones with chiral ligand-modified stable arsonium ylides has been examined. The 8-phenylmenthol-derived chiral arsonium ylide of 4 reacted with prochiral ketones 9a-d at −15°C to give the 4-substituted cyclohexylideneacetates 11a-d in 58–69% yield and in up to 80% diastereomeric excess (de).