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Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst.

Publication ,  Journal Article
Adamson, NJ; Hull, E; Malcolmson, SJ
Published in: Journal of the American Chemical Society
May 2017

We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

May 2017

Volume

139

Issue

21

Start / End Page

7180 / 7183

Related Subject Headings

  • Stereoisomerism
  • Palladium
  • Oxazoles
  • Organometallic Compounds
  • Molecular Structure
  • General Chemistry
  • Catalysis
  • Amines
  • Allyl Compounds
  • Alkadienes
 

Citation

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Adamson, N. J., Hull, E., & Malcolmson, S. J. (2017). Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst. Journal of the American Chemical Society, 139(21), 7180–7183. https://doi.org/10.1021/jacs.7b03480
Adamson, Nathan J., Ethan Hull, and Steven J. Malcolmson. “Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst.Journal of the American Chemical Society 139, no. 21 (May 2017): 7180–83. https://doi.org/10.1021/jacs.7b03480.
Adamson NJ, Hull E, Malcolmson SJ. Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst. Journal of the American Chemical Society. 2017 May;139(21):7180–3.
Adamson, Nathan J., et al. “Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst.Journal of the American Chemical Society, vol. 139, no. 21, May 2017, pp. 7180–83. Epmc, doi:10.1021/jacs.7b03480.
Adamson NJ, Hull E, Malcolmson SJ. Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst. Journal of the American Chemical Society. 2017 May;139(21):7180–7183.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

May 2017

Volume

139

Issue

21

Start / End Page

7180 / 7183

Related Subject Headings

  • Stereoisomerism
  • Palladium
  • Oxazoles
  • Organometallic Compounds
  • Molecular Structure
  • General Chemistry
  • Catalysis
  • Amines
  • Allyl Compounds
  • Alkadienes