Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α-C-Chiral Sulfonamides

被引：25

作者：

Johnson, Michael G. ^{[1
]}

Gribble, Michael W., Jr. ^{[1
]}

Houze, Jonathan B. ^{[1
]}

Paras, Nick A. ^{[1
]}

机构：

[1] Amgen Inc, Dept Therapeut Discovery, 1120 Vet Blvd, San Francisco, CA 94080 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 23期

关键词：

ASYMMETRIC-SYNTHESIS; PYRROLIDINE SULFONAMIDE; MICHAEL ADDITION; EFFICIENT METHOD; SUBSTITUTION; CONDENSATION; NUCLEOPHILES; OXIDATION; ALDEHYDES; REAGENTS;

D O I：

10.1021/ol503208z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthesis of a-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides alpha-C-chiral primary sulfonamides in good yield (14 examples) with retention of stereochemical purity.

引用

页码：6248 / 6251

页数：4

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