Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates

被引：111

作者：

Tao, B

Schlingloff, G

Sharpless, KB

机构：

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

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 17期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

amino acids and derivatives; amino alcohols; asymmetric reactions; catalysis;

D O I：

10.1016/S0040-4039(98)00350-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Use of cinchona ligands with an anthraquinone (AQN) core, in place of the usual phthalazine (PHAL) core, in the asymmetric aminohydroxylation of cinnamates causes dramatic reversal of the regioselection, so that phenyl serines are obtained in high enantiomeric excess. Hence, the regioselectivity outcome (i.e. isoserine vs. serine) is controlled by the ligand and not the substrate. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2507 / 2510

页数：4

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