Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate

被引：1
|
作者：
Lin, Wenhong [1 ]
Meyer, Shea T. [1 ]
Dormann, Shawn [1 ]
Chisholm, John D. [1 ]
机构：
[1] Syracuse Univ, Dept Chem, 1 014 Ctr Sci & Technol, Syracuse, NY 13244 USA
来源：
ORGANICS | 2021年 / 2卷 / 01期
关键词：
esters; beta-silyl carbocations; trichloroacetimidates; protecting groups; C-O bond formation; PROTECTING GROUP; ESTERS; ALKYLATION; SUBSTITUENTS; CONVENIENT; INDOLES;
D O I：
10.3390/org2010002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-(Trimethylsilyl)ethyl 2,2,2-trichloroacetimidate is readily synthesized from 2-trimethylsilylethanol in high yield. This imidate is an effective reagent for the formation of 2-trimethylsilylethyl esters without the need for an exogenous promoter or catalyst, as the carboxylic acid substrate is acidic enough to promote ester formation without an additive. A deuterium labeling study indicated that a beta-silyl carbocation intermediate is involved in the transformation.
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收藏
页码：17 / 25
页数：9
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