Catalytic enantioselective desymmetrization of COT-monoepoxide. Maximum deviation from coplanarity for an S(N)2'-cuprate alkylation.
[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.
Del Moro
Federica
F
Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa.
Crotti
Paolo
P
Di Bussolo
Valeria
V
Macchia
Franco
F
Pineschi
Mauro
M