Synthesis of β-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions

被引：227

作者：

Mase, N

Tanaka, F

Barbas, CF

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

[4] Shizuoka Univ, Dept Mol Sci, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 18期

关键词：

aldol reaction; asymmetric catalysis; enantioselectivity; high-throughput screening; organocatalysis;

D O I：

10.1002/anie.200353546

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A fluorescence detection system was used to identify effective chiral-amine/acid combinations as bifunctional catalysts for asymmetric direct catalytic aldol reactions of α,α-dialkyl aldehydes with aryl aldehydes (see scheme). With the optimized catalyst system, the reaction of isobutyraldehyde with p-nitrobenzaldehyde provided the α,α-dimethyl aldol product in 92% yield with 96% ee. R1, R2 = alkyl; X = NO2, CN, Br, Cl, OMe, H.

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页码：2420 / 2423

页数：4

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