Preparation of bis(β-trimethylsilylethanesulfonyl)imide and its use in the synthesis of protected amine derivatives

被引：12

作者：

Dastrup, DM ^{[1
]}

VanBrunt, MP ^{[1
]}

Weinreb, SM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 10期

关键词：

D O I：

10.1021/jo020754r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis(beta-trimethylsilylethanesulfonyl)imide (SES2-NH) can be easily prepared in 85% yield by alkylation of the trianion of bismethanesulfonimide with 2 equiv of commerically available (iodomethyl)trimethylsilane. This synthon undergoes effective Mitsunobu alkylation reactions with both primary and secondary alcohols to afford the corresponding bis-SES imides. These imides can be selectively cleaved to the mono-SES-protected amines, and in addition undergo a one-pot cleavage/N-alkylation to afford SES derivatives of secondary amines.

引用

页码：4112 / 4115

页数：4

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