"contra-Michael" addition of alkyllithiums to silicon- and phenyl-substituted alpha,beta-unsaturated amides in the presence of t-BuOK

Hinago T; Teshima N; Kenmoku S; Kamata T; Terauchi N; Chiba N; Satoh C; Nakamura A; Asaoka M

Chemistry Letters, Vol.36, No.1, 54-55, 2007

DOI10.1246/cl.2007.54 Export Citation

"contra-Michael" addition of alkyllithiums to silicon- and phenyl-substituted alpha,beta-unsaturated amides in the presence of t-BuOK

Hinago T, Teshima N, Kenmoku S, Kamata T, Terauchi N, Chiba N, Satoh C, Nakamura A, Asaoka M

Carbolithiation of 3-(trimethylsilyl)acrylamide and cinnamamide derivatives gave the corresponding 3-substituted (Michael) and/or 2-substituted (contra-Michael) adducts. The regioselectivity depends on the nature of alkyllithium reagents. In the carbolithiation with n-alkyllithiums, the presence of t-BuOK caused dramatic change of the addition mode and the contra-Michael adducts were obtained exclusively.