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Synthesis of trans-2-(Trifluoromethyl)cyclopropanes via Suzuki Reactions with an N-Methyliminodiacetic Acid Boronate
Organic Letters ( IF 4.9 ) Pub Date : 2013-08-16 00:00:00 , DOI: 10.1021/ol401636d Matthew A. J. Duncton 1 , Rajinder Singh 1
Organic Letters ( IF 4.9 ) Pub Date : 2013-08-16 00:00:00 , DOI: 10.1021/ol401636d Matthew A. J. Duncton 1 , Rajinder Singh 1
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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%).
中文翻译:
N-甲基亚氨基二乙酸硼酸酯的Suzuki反应合成反式-2-(三氟甲基)环丙烷
反式-2-(三氟甲基)环丙基硼酸Ñ -methyliminodiacetic乙酸(MIDA)酯5的合成从乙烯基硼酸MIDA酯和(三氟甲基)重氮甲烷在单个步骤中的纯非对映体。X射线研究证实了环丙基环周围的反式立体化学。在Suzuki反应中使用5和各种芳基或杂芳基偶合伙伴,可提供中等至极好的收率(17-90%)的反式-2-(三氟甲基)环丙基产品。
更新日期:2013-08-16
中文翻译:
N-甲基亚氨基二乙酸硼酸酯的Suzuki反应合成反式-2-(三氟甲基)环丙烷
反式-2-(三氟甲基)环丙基硼酸Ñ -methyliminodiacetic乙酸(MIDA)酯5的合成从乙烯基硼酸MIDA酯和(三氟甲基)重氮甲烷在单个步骤中的纯非对映体。X射线研究证实了环丙基环周围的反式立体化学。在Suzuki反应中使用5和各种芳基或杂芳基偶合伙伴,可提供中等至极好的收率(17-90%)的反式-2-(三氟甲基)环丙基产品。