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Issue 13, 2018
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Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration

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Abstract

Tri- and tetrasubstituted allenylboronic acids were prepared via a new versatile copper-catalyzed methodology. The densely functionalized allenylboronic acids readily undergo propargylboration reactions with ketones and imines without any additives. Catalytic asymmetric propargylborylation of ketones is demonstrated with high stereoselectivity allowing for the synthesis of highly enantioenriched tertiary homopropargyl alcohols. The reaction is suitable for kinetic resolution of racemic allenylboronic acids affording alkynes with adjacent quaternary stereocenters.

Graphical abstract: Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration

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Publication details

The article was received on 01 Dec 2017, accepted on 17 Feb 2018 and first published on 19 Feb 2018


Article type: Edge Article
DOI: 10.1039/C7SC05123A
Citation: Chem. Sci., 2018,9, 3305-3312
  • Open access: Creative Commons BY license
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    Copper-catalyzed synthesis of allenylboronic acids. Access to sterically encumbered homopropargylic alcohols and amines by propargylboration

    J. Zhao, S. J. T. Jonker, D. N. Meyer, G. Schulz, C. D. Tran, L. Eriksson and K. J. Szabó, Chem. Sci., 2018, 9, 3305
    DOI: 10.1039/C7SC05123A

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