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
收藏
页码：2723 / 2734
页数：12
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