Highly Enantioselective Regiodivergent and Catalytic Parallel Kinetic Resolution This work was supported by the Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST, Roma) and by the University of Pisa. We gratefully acknowledge Merck for the generous financial support derived from the 2000 ADP Chemistry Award.

Abstract

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.