Mechanism of an Organoboron-Catalyzed Domino Reaction: Kinetic and Computational Studies of Borinic Acid-Catalyzed Regioselective Chloroacylation of 2,3-Epoxy Alcohols

• Published in: Journal of organic chemistry Vol. 82; no. 2; pp. 1085 - 1095
• Main Authors: Garrett, Graham E, Tanveer, Kashif, Taylor, Mark S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.01.2017; Amer Chemical Soc
• Subjects: acylation; alcohols; catalysts; catalytic activity; chemical structure; Chemistry; Chemistry, Organic; chlorides; Fourier transform infrared spectroscopy; kinetics; Lewis acids; Lewis bases; organic chemistry; Physical Sciences; regioselectivity; Science & Technology; DIOLS; METHODOLOGY; ENTRY; RECOGNITION; SN2; NUCLEOPHILIC-SUBSTITUTION; TRIGONAL CARBON; TUNGSTEN; DERIVATIVES; CHLORIDE

A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid activates the substrate toward sequential reactions with a nucleophile (epoxide ring-opening by chloride) and an electrophile (O-acylation of the...