title: Copper-catalyzed divergent kinetic resolution of racemic allylic substrates.
abstract: When a racemic mixture is fully consumed the products may still be enantiomerically enriched. In particular, the regiodivergent kinetic resolution is a process in which a single chiral catalyst or reagent reacts with a racemic substrate to form regioisomers possessing an opposite configuration on the newly-formed stereogenic centers. This review reports the major advances in the field of the copper-catalyzed regiodivergent and stereodivergent kinetic resolution of allylic substrates with organometallic reagents. The chiral recognition matching phenomena found with particular allylic substrates with the absolute configuration of the chiral catalyst allows in some cases an excellent control of the regio- and stereoselectivity, sheding some light on the so-called "black-box" mechanism of a copper-catalyzed asymmetric allylic alkylation.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, Pisa, Italy. pineschi@farm.unipi.it
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D004852:Epoxy Compounds; D009942:Organometallic Compounds; D003300:Copper