Pd-Catalyzed Allylic Alkylation of gem-Alkyl,Aryl-Disubstituted Allyl Reagents with Ketones: Diastereoselective Construction of Vicinal Tertiary and Quaternary Carbon Centers
ACS Catalysis2018Vol. 8(4), pp. 3317–3321
Citations Over TimeTop 20% of 2018 papers
Abstract
(E)-gem-Alkyl,aryl-disubstituted allyl carbonates can react with ketones under Pd catalysis using a commercially available NHC ligand by suppressing the β-H elimination. Ketones with α-tertiary, β-quaternary carbon stereocenters were produced in high yields with high regio- and diastereoselectivities. Kinetic resolution of the reaction product via CBS reduction afforded the optically active ketone as well as the alcohol with high enantioselectivity (S-factor = 35). The utility of the methodology was also demonstrated by transformations of the reaction products.
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