Consecutive borylcupration/C–C coupling of γ-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols
Ricardo J. Maza, Jordi Royes, Jorge J. Carbó, Elena Fernández
Abstract
Copper(i) catalyzes the borylative cyclization of γ-alkenyl aldehydes through chemo- and regioselective addition of Cu-B to C[double bond, length as m-dash]C and concomitant intramolecular 1,2-addition of Cu-C on C[double bond, length as m-dash]O. The products are formed in an exclusive diastereoselective manner and computational analysis identifies the key points for the observed chemo- and diastereoselectivity.
Topics & Concepts
RegioselectivityChemistryIntramolecular forceDouble bondMedicinal chemistryStereochemistryOrganic chemistryCatalysisOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions