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Enantioselective Palladium-Catalyzed Diboration of 1,1-Disubstituted Allenes

Abstract

A practical and enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes is developed by employing a P-chiral monophosphorus ligand BI-DIME to form a series of diboronic esters containing a chiral tertiary boronic ester moiety in excellent yields and ee’s with the palladium loading as low as 0.2 mol %. DFT calculations revealed a concerted mechanism of oxidative addition of bis(pinacolato)diboron and allene insertion, as well as a critical dispersion effect on the origins of the enantioselectivity. The method is successfully applied to a concise and enantioselective synthesis of brassinazole.

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Publication details

The article was received on 20 Mar 2017, accepted on 07 May 2017 and first published on 16 May 2017


Article type: Edge Article
DOI: 10.1039/C7SC01254C
Citation: Chem. Sci., 2017, Accepted Manuscript
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    Enantioselective Palladium-Catalyzed Diboration of 1,1-Disubstituted Allenes

    W. Tang, J. Liu, M. Nie, Q. Zhou, S. Gao, W. Jiang, L. W. Chung and K. Ding, Chem. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C7SC01254C

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