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Issue 19, 2019
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Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes

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Abstract

We describe the development of Pd–PHOX-catalysed enantioselective couplings of internal dienes with malononitrile and other activated C-pronucleophiles. Reactions are dramatically accelerated by the addition of Et3N·HBArF4 as a Brønsted acid co-catalyst, enabling a suite of products bearing a variety of alkyl substituents at the stereogenic carbon to be prepared. A series of mechanism-oriented experiments reveal key aspects of the catalytic cycle and the importance of the non-coordinating BArF4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes.

Graphical abstract: Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes

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Publication details

The article was received on 04 Feb 2019, accepted on 16 Apr 2019 and first published on 17 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC00633H
Chem. Sci., 2019,10, 5176-5182
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes

    S. Park, N. J. Adamson and S. J. Malcolmson, Chem. Sci., 2019, 10, 5176
    DOI: 10.1039/C9SC00633H

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