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Development and Mechanistic Investigations of Enantioselective Pd-Catalyzed Intermolecular Hydroaminations of Internal Dienes

Publication ,  Journal Article
Park, S; Malcolmson, SJ
Published in: ACS Catalysis
September 7, 2018

We report the development of highly enantio- and regioselective Pd-catalyzed intermolecular hydroaminations of challenging 1,4-disubstituted acyclic dienes. Several aryl/alkyl-disubstituted dienes and a sterically differentiated alkyl/alkyl-disubstituted diene undergo coupling with a variety of secondary aliphatic amines, indoline, and primary anilines to generate allylic amines with myriad α-alkyl groups in up to 78% yield, >98:2 rr, and 98.5:1.5 er. A number of experiments, including deuterium labeling and transamination studies, shed light on mechanistic details of the reaction, such as the reversibility of individual steps of the proposed catalytic cycle and of the reaction as a whole.

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Published In

ACS Catalysis

DOI

EISSN

2155-5435

Publication Date

September 7, 2018

Volume

8

Issue

9

Start / End Page

8468 / 8476

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

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Park, S., & Malcolmson, S. J. (2018). Development and Mechanistic Investigations of Enantioselective Pd-Catalyzed Intermolecular Hydroaminations of Internal Dienes. ACS Catalysis, 8(9), 8468–8476. https://doi.org/10.1021/acscatal.8b01914
Park, S., and S. J. Malcolmson. “Development and Mechanistic Investigations of Enantioselective Pd-Catalyzed Intermolecular Hydroaminations of Internal Dienes.” ACS Catalysis 8, no. 9 (September 7, 2018): 8468–76. https://doi.org/10.1021/acscatal.8b01914.
Park, S., and S. J. Malcolmson. “Development and Mechanistic Investigations of Enantioselective Pd-Catalyzed Intermolecular Hydroaminations of Internal Dienes.” ACS Catalysis, vol. 8, no. 9, Sept. 2018, pp. 8468–76. Scopus, doi:10.1021/acscatal.8b01914.
Journal cover image

Published In

ACS Catalysis

DOI

EISSN

2155-5435

Publication Date

September 7, 2018

Volume

8

Issue

9

Start / End Page

8468 / 8476

Related Subject Headings

  • 3406 Physical chemistry
  • 3405 Organic chemistry
  • 3106 Industrial biotechnology
  • 0904 Chemical Engineering
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry