DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-TRIALKYLSTANNYLCYCLOHEXANONES BY MICHAEL ADDITION OF TRIALKYLSTANNYLLITHIUM TO CYCLOHEXENONE SAMP HYDRAZONE

Overall yields of up to 80% are achieved in the Michael addition of trialkylstannyllithium to cyclohexenone SAMP hydrazone (S)‐1 (or its R enantiomer) followed by α‐alkylation. This tandem reaction provides, after oxidative cleavage of the auxiliary, 2‐substituted trans‐3‐trialkylstannylcyclohexanones (S,S)2 (and the enantiomers (R,R)‐2) in high enantiomeric purity (de ≥ 98%, ee 85 to ≥ 96%). R1, R2 are for example, nBu, Me. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany