The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

被引：46

作者：

Aggarwal, Varinder K. ^{[1
]}

Barbero, Nekane ^{[1
]}

McGarrigle, Eoghan M. ^{[1
]}

Mickle, Greg ^{[1
]}

Navas, Raquel ^{[1
]}

Suarez, Jose Ramon ^{[1
]}

Unthank, Matthew G. ^{[1
]}

Yar, Muhammad ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

Ellman's auxiliary; tert-Butylsulfinamide; Sulfinimines; Deprotection; Cleavage; Dynamic kinetic resolution; DYNAMIC KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; SULFINYL CHLORIDES; BUTANESULFINYL IMINES; SULFINIMINES; COMBINATIONS; SULFINAMIDES; SULFOXIDES; ESTERS; DAG;

D O I：

10.1016/j.tetlet.2009.03.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3482 / 3484

页数：3

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