The stereochemistry of the Grignard reaction of steroidal 4,5-epoxy-3-ketones

The stereochemistry of the addition of methylmagnesium bromide to a steroidal 4,5-epoxy-3-ketone has been shown to be determined by the stereochemistry of the epoxide. The epoxidation to the corresponding 3-alkyl-3-hydroxy-4-enes by per-acid was determined by the stereochemistry of the allylic alcohol.