a Department of Chemistry, DePauw University, Greencastle, IN 46135, USA b Department of Chemistry, Indiana University, Bloomington, IN 47405, USA
Abstract:
A mixture of cyclohexanone or 4-methylcyclohexanone and an aromatic aldehyde is treated with dimethylsulfoxonium methylide to effect a tandem aldol/epoxidation reaction. The resulting product contains three or four new stereocenters but only one of the possible four or eight diastereomers is formed.