title: Synthesis of trans-2-(trifluoromethyl)cyclopropanes via Suzuki reactions with an N-methyliminodiacetic acid boronate.
abstract: 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%).
authors: Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, USA. mduncton@rigel.com
authors: Matthew A J
authors: MA
authors: Duncton
authors: Rajinder
authors: R
authors: Singh
mesh_terms: D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007098:Imino Acids / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D003521:Cyclopropanes; D004952:Esters; D006845:Hydrocarbons, Fluorinated; D007098:Imino Acids; C533766:N-methyliminodiacetic acid; C586344:trans-2-(trifluoromethyl)cyclopropylboronic acid N-methyliminodiacetic acid; D010165:Palladium