Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution

Chiral recognition leads to enantio- and regiodivergent reactivity: An unusual regiodivergent catalytic kinetic resolution has been accomplished for the first time in an organometallic reaction in which a C−C bond is formed. Chiral copper complexes of the non-racemic phosphoramidite ligand L* discriminate the enantiomers of semirigid vinyloxiranes (having a blocked s-cis or s-trans conformation) to give separable regioisomeric products with very high stereocontrol in a two-step process (see scheme).