THE MATTESON REACTION

摘要

The Matteson reaction is the nucleophilic displacement of any suitable leaving group from the α-carbon of an alkylboronic ester. Its serendipitous discovery occurred shortly after the first (α-bromoalkyl)boronic ester was prepared by the radical addition of bromotrichloromethane to dibutyl vinylboronate. The Matteson reaction became a broadly useful method in asymmetric synthesis when it was discovered that boronate complexes formed from the addition of (dichloromethyl)lithium to boronic esters of diols undergo an efficient 1,2-metallate transposition to (α-chloroalkyl)boronic esters, and that boronic esters of the diol derived from α-pinene afford highly diastereomerically enriched products.