Enantioselective Catalysts for the Synthesis of α-Substituted Allylboronates--An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols

Abstract

The use of a convenient protecting group for boronates allows a selective, catalyzed S(N)2' reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.

Keywords: allylation; asymmetric catalysis; asymmetric synthesis; boron; computational chemistry.