title: Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation.
abstract: [reaction: see text] The first alkylative and enantioselective ring-opening of COT-monoepoxide (1) without the occurrence of any ring-contraction-isomerization by the use of in situ-formed organocuprates is reported. Because of the particular geometric constraint of compound 1, this work reports the largest deviation from coplanarity between the pi-orbital of the double bond and the sigma-bond connecting the leaving group ever observed for an S(N)2'-cuprate alkylation.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa.
authors.forename: Federica
authors.initials: F
authors.lastname: Del Moro
authors.forename: Paolo
authors.initials: P
authors.lastname: Crotti
authors.forename: Valeria
authors.initials: V
authors.lastname: Di Bussolo
authors.forename: Franco
authors.initials: F
authors.lastname: Macchia
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi