Cross-coupling reactions of alkyl electrophiles catalyzed by chiral metal complexes are potentially powerful tools for enantioselective carbon�carbon bond formation.  Previous disclosures from our laboratory include the first example of an asymmetric Suzuki-Miyaura reaction of unactivated secondary halides. In an extension of this concept, Scheme 1 outlines a protocol whereby an acyl-protected halohydrin undergoes a stereoconvergent cross-coupling reaction with an alkylborane, allowing access to the corresponding chiral alcohols. Studies into the scope and applications of this methodology will be discussed. 

Enantioselective alkyl-alkyl Suzuki-Miyaura cross-couplings of acylated alcohols

239th National Meeting (2010)

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