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

Article abstract of DOI:10.1016/S0957-4166(97)00223-1

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).