Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones 英文参考文献.docVIP

Symmetry 2011, 3, 155-164; doi:10.3390/sym3020155 OPEN ACCESS symmetry ISSN 2073-8994 /journal/symmetry Article Primary Amino Acid Lithium Salt-Catalyzed Asymmetric Michael Addition of Carbon Nucleophiles to Enones Masanori Yoshida *, Keisuke Hirama, Mao Narita and Shoji Hara Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan; E-Mails: lor@eng.hokudai.ac.jp (K.H. and M.N.); shara@eng.hokudai.ac.jp (S.H.) * Author to whom correspondence should be addressed; E-Mail: myoshida@eng.hokudai.ac.jp. Received: 18 February 2011; in revised form: 6 April 2011 / Accepted: 7 April 2011 / Published: 8 April 2011 Abstract: Asymmetric Michael addition of carbon nucleophiles, nitroalkanes and a β-ketoester, to enones was investigated by using a primary amino acid lithium salt as a catalyst. Keywords: amino acid; asymmetric synthesis; organocatalysis; michael addition 1. Introduction Michael addition of carbon nucleophiles to α,β-unsaturated carbonyl compounds is one of the most important synthetic methodologies to create a new carbon-carbon bond at the β-position of the carbonyl group. In the case of obtaining a Michael adduct enantioselectively, organocatalytic asymmetric synthesis has been recognized as an important candidate, as a result of explosive growth of organocatalysis in the past decade [1–5]. As pioneering works in organocatalytic asymmetric Michael addition of carbon nucleophiles to α,β-unsaturated carbonyl compounds, Yamaguchi’s group reported that Michael addition of malonates to enones could be catalyzed by a proline alkali metal salt [6–12]. They later succeeded in the asymmetric Michael addition of nitroalkanes to enones using a proline rubidium salt-catalyst [13–32]. We recently reported that an O-silylated L-serine lithium salt was an effective catalyst for asymmetr