Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes

JR Coombs, F Haeffner, LT Kliman…

Index: Coombs, John R.; Haeffner, Fredrik; Kliman, Laura T.; Morken, James P. Journal of the American Chemical Society, 2013 , vol. 135, # 30 p. 11222 - 11231

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Citation Number: 34

Abstract

The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion into a Pt–B bond. Density functional theory ...