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

Publication ,  Journal Article
Park, S; Adamson, NJ; Malcolmson, SJ
Published in: Chemical science
May 2019

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·HBArF 4 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 BArF 4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes.

Duke Scholars

Published In

Chemical science

DOI

EISSN

2041-6539

ISSN

2041-6520

Publication Date

May 2019

Volume

10

Issue

19

Start / End Page

5176 / 5182

Related Subject Headings

  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Park, S., Adamson, N. J., & Malcolmson, S. J. (2019). Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes. Chemical Science, 10(19), 5176–5182. https://doi.org/10.1039/c9sc00633h
Park, Sangjune, Nathan J. Adamson, and Steven J. Malcolmson. “Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.Chemical Science 10, no. 19 (May 2019): 5176–82. https://doi.org/10.1039/c9sc00633h.
Park S, Adamson NJ, Malcolmson SJ. Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes. Chemical science. 2019 May;10(19):5176–82.
Park, Sangjune, et al. “Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.Chemical Science, vol. 10, no. 19, May 2019, pp. 5176–82. Epmc, doi:10.1039/c9sc00633h.
Park S, Adamson NJ, Malcolmson SJ. Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes. Chemical science. 2019 May;10(19):5176–5182.
Journal cover image

Published In

Chemical science

DOI

EISSN

2041-6539

ISSN

2041-6520

Publication Date

May 2019

Volume

10

Issue

19

Start / End Page

5176 / 5182

Related Subject Headings

  • 34 Chemical sciences
  • 03 Chemical Sciences