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Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

Publication ,  Journal Article
Adamson, NJ; Wilbur, KCE; Malcolmson, SJ
Published in: Journal of the American Chemical Society
February 2018

We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

February 2018

Volume

140

Issue

8

Start / End Page

2761 / 2764

Related Subject Headings

  • Temperature
  • Stereoisomerism
  • Palladium
  • Nitriles
  • Molecular Structure
  • Ketones
  • General Chemistry
  • Catalysis
  • Alkylation
  • Alkadienes
 

Citation

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ICMJE
MLA
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Adamson, N. J., Wilbur, K. C. E., & Malcolmson, S. J. (2018). Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society, 140(8), 2761–2764. https://doi.org/10.1021/jacs.7b13300
Adamson, Nathan J., Katherine C. E. Wilbur, and Steven J. Malcolmson. “Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.Journal of the American Chemical Society 140, no. 8 (February 2018): 2761–64. https://doi.org/10.1021/jacs.7b13300.
Adamson NJ, Wilbur KCE, Malcolmson SJ. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society. 2018 Feb;140(8):2761–4.
Adamson, Nathan J., et al. “Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.Journal of the American Chemical Society, vol. 140, no. 8, Feb. 2018, pp. 2761–64. Epmc, doi:10.1021/jacs.7b13300.
Adamson NJ, Wilbur KCE, Malcolmson SJ. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles. Journal of the American Chemical Society. 2018 Feb;140(8):2761–2764.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

February 2018

Volume

140

Issue

8

Start / End Page

2761 / 2764

Related Subject Headings

  • Temperature
  • Stereoisomerism
  • Palladium
  • Nitriles
  • Molecular Structure
  • Ketones
  • General Chemistry
  • Catalysis
  • Alkylation
  • Alkadienes