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Issue 7, 2017
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Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes

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Abstract

A practical and enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes is developed by employing a P-chiral monophosphorus ligand, BI-DIME. A series of diboronic esters containing a chiral tertiary boronic ester moiety are formed 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 the concise and enantioselective synthesis of brassinazole.

Graphical abstract: Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes

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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., 2017,8, 5161-5165
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    Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes

    J. Liu, M. Nie, Q. Zhou, S. Gao, W. Jiang, L. W. Chung, W. Tang and K. Ding, Chem. Sci., 2017, 8, 5161
    DOI: 10.1039/C7SC01254C

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