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Paper | Special issue | Vol 79, No. 1, 2009, pp.573-582
Published online, 30th October, 2008
DOI: 10.3987/COM-08-S(D)18
Asymmetric Synthesis of 4-Substituted 2,6-Dioxopiperidine-3-carbonitrile by Using Thiourea-Catalyzed Asymmetric Michael Addition

Tsubasa Inokuma, Yuuki Nagamoto, Shota Sakamoto, Hideto Miyabe, Kiyosei Takasu, and Yoshiji Takemoto*

*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

An enantioselective Michael addition of several α,β-unsaturated carbonyl compounds with malononitrile catalyzed by a bifunctional thiourea is described. We also demonstrate the transformation of Michael adduct into an enantiomerically enriched functionalized piperidine.