Synthesis of trans-2-(Trifluoromethyl)cyclopropanes via Suzuki Reactions with an N-Methyliminodiacetic Acid Boronate

被引：59

作者：

Duncton, Matthew A. J. ^{[1
]}

Singh, Rajinder ^{[1
]}

机构：

[1] Rigel Inc, San Francisco, CA 94080 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 17期

关键词：

SMALL-MOLECULE SYNTHESIS; MEDICINAL CHEMISTRY; CYCLOPROPANE DERIVATIVES; STRATEGY; COMPLEXITY; FRAMEWORKS; DISCOVERY;

D O I：

10.1021/ol401636d

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

trans-2-(Trifluoromethyl)cyclopropylboronic acid N-methyliminodiacetic acid (MIDA) ester 5 was synthesized as a pure diastereomer from vinylboronic acid MIDA ester and (trifluoromethyl)diazomethane in a single step. An X-ray study confirmed the trans-stereochemistry around the cyclopropyl ring. Use of 5 in Suzuki reactions, with a variety of aryl or heteroaryl coupling partners, provided trans-2-(trifluoromethyl)cyclopropyl products in moderate to excellent yields (17-90%).

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收藏

页码：4284 / 4287

页数：4

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