Phase-transfer-catalyzed enantioselective Mannich reaction of malonates with α-amido sulfones

被引：72

作者：

Fini, Francesco ^{[1
]}

Bernardi, Luca ^{[1
]}

Herrera, Raquel P. ^{[1
]}

Pettersen, Daniel ^{[1
]}

Ricci, Alfredo ^{[1
]}

Sgarzani, Valentina ^{[1
]}

机构：

[1] Univ Bologna, Dept Organ Chem A Mangini, I-40136 Bologna, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 15期

关键词：

alpha-amido sulfones; asymmetric synthesis; Mannich reaction; nucleophilic addition; phase-transfer catalysis;

D O I：

10.1002/adsc.200600250

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The highly enantioselective reaction between in situ generated, Cbz-protected azomethines and malonates in the presence of 150 mol % of potassium carbonate (50 % w/w) and 1 mol % of quinine-derived quaternary ammonium bromides as phase-transfer organocatalysts has been developed. This study reports a novel approach for the asymmetric Mannich-type reaction and a wide range of azomethines, including those derived from enolizable aldehydes, is tolerated by the present system. The adducts, obtained in excellent yields with ee up to 98 %, are suitable precursors of optically pure amino acids.

引用

页码：2043 / 2046

页数：4

共 43 条

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