Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes:: Step one in a two-step synthesis of carbohydrates

被引：289

作者：

Northrup, AB ^{[1
]}

Mangion, IK ^{[1
]}

Hettche, F ^{[1
]}

MacMillan, DWC ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 16期

关键词：

aldehydes; aldol reaction; carbohydrates; enantioselectivity; homogeneous catalysis;

D O I：

10.1002/anie.200453716

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereo-controlled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.

引用

页码：2152 / 2154

页数：3

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