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

被引：55
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 ; 081704 ;
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%).
引用
收藏
页码：4284 / 4287
页数：4
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