A convenient synthesis of piperidine-based β-amino alcohols from L-Phe and highly enantioselective addition of diethyl zinc to aldehydes

被引：50

作者：

Da, CS ^{[1
]}

Han, ZJ ^{[1
]}

Ni, M ^{[1
]}

Yang, F ^{[1
]}

Liu, DX ^{[1
]}

Zhou, YF ^{[1
]}

Wang, R ^{[1
]}

机构：

[1] Lanzhou Univ, Sch Life Sci, Dept Biochem & Mol Biol, Lanzhou 730000, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 06期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/S0957-4166(03)00122-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

beta-Amino alcohols 4a-e were easily prepared from L-phenylalanine. in three simple straightforward steps. The key intermediate compound (S)-3 was achieved in high yield (up to 92%) with glutaraldehyde and NaBH4/H2SO4 in THF at room temperature. These five ligands were applied to catalyze enantioselective addition of diethyl zinc to aldehydes, high asymmetric induction was observed with 4c and 4e, and the ee value was up to 98%. The effect of the substitutes on the nitrogen atom was also observed via comparing piperidine-based amino alcohols with pyrrolidine-based similar ligands. (0 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：659 / 665

页数：7

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