Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane

被引：23
作者：
Astakhova, Vera V. [1 ]
Moskalik, Mikhail Yu. [1 ]
Shainyan, Bagrat A. [1 ]
机构：
[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 34期
关键词：
CATALYST-FREE; STEREOSELECTIVE AMINOBROMINATION; NITROGEN; OLEFINS; TSNH2; AZIRIDINATION; EFFICIENT; ALKENES; KETONES; AMINOHALOGENATION;
D O I：
10.1039/c9ob01689a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of trimethyl(vinyl)silane with sulfonamides in the presence of N-bromosuccinimide was shown to proceed regioselectively in methylene chloride under mild conditions and led to the products of bromosulfamidation in up to 88% yield. The obtained adducts undergo base-promoted dehydrobromination to give 2-trimethylsilyl-N-sulfonyl aziridines in a close to quantitative yield. In the reaction with trifluoromethanesulfonamide in acetonitrile or tetrahydrofuran, the Ritter-type (solvent-interception) products were obtained and converted to 1-triflyl-2-methyl-5-(trimethylsilyl)-2-imidazoline or 4-triflyl-3-(trimethylsilyl)-1,4-oxazocane in almost quantitative yield.
引用
收藏
页码：7927 / 7937
页数：11
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