Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
Chenlong Zhang, Weipeng Hu, Gabriel J. Lovinger, Jing Jin, Jingjia Chen, James P. Morken
Abstract
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
Topics & Concepts
ChemistryReagentEnantioselective synthesisStereospecificityCatalysisNickelOrganic chemistryCombinatorial chemistryOrganoboron and organosilicon chemistryAsymmetric Synthesis and CatalysisCoordination Chemistry and Organometallics