Stereoselective synthesis of α-hydroxy-β-amino acid derivatives from β-hydroxy-γ,δ-unsaturated sulfilimine

被引：13

作者：

Raghavan, Sadagopan ^{[1
]}

Mustafa, Shalk ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500 007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 20期

关键词：

N-sulfinyl benzylcarbamate; sulfoxide; N-Cbz sulfilimine; bromo carbamate; (2S; 3R)-AHDA; 3R)-AHPBA;

D O I：

10.1016/j.tetlet.2008.03.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first report on the use of N-sulfinyl benzylcarbamate for the preparation of N-Cbz sulfilimine from the corresponding sulfoxide is reported. The sulfilimine moiety is utilized as an intramolecular nucleophile for the regio- and stereoselective heterofunctionalization of an alkene to furnish a bromo carbamate which is used as a key advanced intermediate in the synthesis of representative alpha-hydroxy-beta-amino acid derivatives. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3216 / 3220

页数：5

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