S-Allyl Thiocarbamates from Allylic Alcohols by in situ [3,3]-Sigmatropic Rearrangement of a Thiocarbonyldiimidazole Adduct

被引：3

作者：

Mingat, Gaelle ^{[1
]}

Clayden, Jonathan ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

sigmatropic rearrangement; thiocarbamates; alcohols; stereospecificity; sulfur; ALPHA-ARYLATION; CONFIGURATIONAL STABILITY; STEREOCHEMICAL COURSE; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; CARBON-MONOXIDE; AMINES; SULFUR; CALICHEAMICIN-GAMMA-1(I); CONVERSION;

D O I：

10.1055/s-0032-1316746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of allylic alcohols with thiocarbonyldiimidazole generates an unstable O-allyl imidazolyl thione ester, which rearranges spontaneously and in high yield to the corresponding S-allyl imidazolyl thiol ester. Displacement of the imidazole by N-alkylanilines in the presence of a nucleophilic catalyst (HOBt or ECHIA) gives S-allyl N-aryl thiocarbamates in excellent yields (up to 97%) over two steps.

引用

页码：2723 / 2734

页数：12

共 18 条

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