Direct asymmetric aldol reactions of glycine Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts

被引：0

作者：

Ooi, T ^{[1
]}

Taniguchi, M ^{[1
]}

Kameda, M ^{[1
]}

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2002年 / 41卷 / 23期

关键词：

aldol reactions; amino acids; asymmetric synthesis; phase-transfer catalysis; Schiff bases;

D O I：

10.1002/1521-3773(20021202)41:23<4542::AID-ANIE4542>3.0.CO;2-3

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical and environmentally benign chemical process for the synthesis of optically active β-hydroxy-α-amino acids involves the reaction of an aldehyde, glycine Schiff base 2, in the presence of catalytic N-spiro chiral quaternary ammonium bromide 1, The cross-aldol product 3 is obtained with excellent stereochemical control (see scheme; a) (R,R)-1 (2 mol%), toluene/aqueous NaOH (1 %), 0°C, 2 h; b) HCl (1N)/THF).

引用

页码：4542 / +

页数：4

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