手性 β-氨基酸及其锂盐催化的丙二酸盐与烯酮的不对称迈克尔加成反应。

Asymmetric Michael addition of malonates to enones catalyzed by a primary β-amino acid and its lithium salt.

机构信息

Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan.

出版信息

J Org Chem. 2011 Oct 21;76(20):8513-7. doi: 10.1021/jo201429w. Epub 2011 Sep 16.

DOI:10.1021/jo201429w

Abstract

Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary β-amino acid, O-TBDPS (S)-β-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization of the reaction conditions for the Michael addition reaction, and a plausible reaction mechanism are described.

摘要

使用由伯氨基氨基酸、O-TBDPS（S）-β-高丝氨酸及其锂盐组成的混合催化剂，实现了丙二酸酯对烯酮的高对映选择性迈克尔加成。在温和的反应条件下，各种环状和非环状烯酮在高收率（高达 92%）和高对映选择性（高达 97%ee）下转化为 1,5-二酮酯。描述了催化剂的合成细节、迈克尔加成反应条件的优化以及合理的反应机理。

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