Asymmetric Michael addition of malonate anions to prochiral acceptors catalyzed by L-proline rubidium salt

M Yamaguchi, T Shiraishi…

Index: Yamaguchi, Masahiko; Shiraishi, Tai; Hirama, Masahiro Journal of Organic Chemistry, 1996 , vol. 61, # 10 p. 3520 - 3530

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Citation Number: 248

Abstract

l-Proline rubidium salt catalyzes the asymmetric Michael addition of malonate anions to prochiral enones and enals. This method can be applied to a wide range of substrates to give adducts with a predictable absolute configuration:(S)-adducts from (E)-enones/enals and (R)-adducts from cyclic (Z)-enones. Both the secondary amine moiety and the carboxylate moiety are critical for the catalytic activity and asymmetric induction. Varying ...