Diastereoselective sulfur ylide promoted aldol/epoxidation

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.

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