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Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Publication ,  Journal Article
Adamson, NJ; Jeddi, H; Malcolmson, SJ
Published in: Journal of the American Chemical Society
May 2019

In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

May 2019

Volume

141

Issue

21

Start / End Page

8574 / 8583

Related Subject Headings

  • Stereoisomerism
  • Palladium
  • Molecular Structure
  • General Chemistry
  • Catalysis
  • Amination
  • Alkynes
  • Alkadienes
  • 40 Engineering
  • 34 Chemical sciences
 

Citation

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Adamson, N. J., Jeddi, H., & Malcolmson, S. J. (2019). Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design. Journal of the American Chemical Society, 141(21), 8574–8583. https://doi.org/10.1021/jacs.9b02637
Adamson, Nathan J., Haleh Jeddi, and Steven J. Malcolmson. “Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.Journal of the American Chemical Society 141, no. 21 (May 2019): 8574–83. https://doi.org/10.1021/jacs.9b02637.
Adamson NJ, Jeddi H, Malcolmson SJ. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design. Journal of the American Chemical Society. 2019 May;141(21):8574–83.
Adamson, Nathan J., et al. “Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.Journal of the American Chemical Society, vol. 141, no. 21, May 2019, pp. 8574–83. Epmc, doi:10.1021/jacs.9b02637.
Adamson NJ, Jeddi H, Malcolmson SJ. Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design. Journal of the American Chemical Society. 2019 May;141(21):8574–8583.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

May 2019

Volume

141

Issue

21

Start / End Page

8574 / 8583

Related Subject Headings

  • Stereoisomerism
  • Palladium
  • Molecular Structure
  • General Chemistry
  • Catalysis
  • Amination
  • Alkynes
  • Alkadienes
  • 40 Engineering
  • 34 Chemical sciences