Highly Stereoselective Addition of Organometallic Reagents to N-tert-Butanesulfinyl Imines Derived from 3- and 4-Substituted Cyclohexanones

Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group stereochemistry, and therefore racemic tert-butanesulfinamide can be employed.