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.

引用

页码：17 / 25

页数：9

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