Catalytic Asymmetric Protonation of Chiral Calcium Enolates via 1,4-Addition of Malonates

被引：58

作者：

Poisson, Thomas

Yamashita, Yasuhiro

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Japan Sci & Technol Agcy, ERATO, HFRE Div,Sch Sci,Dept Chem,Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 23期

关键词：

SYNTHESEN MIT KETENEN; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE PROTONATION; 1,4-ADDITION/ENANTIOSELECTIVE PROTONATION; ORGANISCHE KATALYSATOREN; BETA(2)-AMINO ACIDS; CONJUGATE ADDITIONS; MICHAEL ADDITIONS; ATOM TRANSFER; COMPLEXES;

D O I：

10.1021/ja102555a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric protonation of chiral calcium enolates was performed. Chiral calcium enolates, prepared in situ from imides and malonates via 1,4-addition in the presence of catalytic amounts of Ca(OEt)(2), Ph-PyBox, and achiral phenol, were smoothly protonated to afford adducts bearing tertiary asymmetric carbons in high yields with high enantioselectivities. The adducts were readily converted to optically active 2-substituted 1,5-dicarboxylic acid derivatives.

引用

页码：7890 / +

页数：4

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