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Catalytic Enantio- And Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes

Publication ,  Journal Article
Adamson, NJ; Malcolmson, SJ
Published in: ACS Catalysis
January 17, 2020

Catalytic enantioselective synthesis of small-molecule building blocks with allylic stereogenic centers is an important objective in organic synthesis, but preparing this motif wherein the adjacent olefin is 1,2-disubstituted in a single step is a tremendous challenge. Late-transition-metal-catalyzed intermolecular couplings of nucleophiles and 1,3-dienes in hydrofunctionalization reactions have quickly emerged as a compelling approach to these and related compounds. In this Perspective, we illustrate how these intermolecular diene hydrofunctionalizations have provided an avenue to complex, highly desirable chemical space that is not readily accessed by other technologies. We also aim to provide some insight into the varying mechanistic pathways and nuances of these myriad reactions to help inform future reaction and catalyst design.

Duke Scholars

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Published In

ACS Catalysis

DOI

EISSN

2155-5435

Publication Date

January 17, 2020

Volume

10

Issue

2

Start / End Page

1060 / 1076

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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Adamson, N. J., & Malcolmson, S. J. (2020). Catalytic Enantio- And Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes. ACS Catalysis, 10(2), 1060–1076. https://doi.org/10.1021/acscatal.9b04712
Adamson, N. J., and S. J. Malcolmson. “Catalytic Enantio- And Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes.” ACS Catalysis 10, no. 2 (January 17, 2020): 1060–76. https://doi.org/10.1021/acscatal.9b04712.
Adamson, N. J., and S. J. Malcolmson. “Catalytic Enantio- And Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes.” ACS Catalysis, vol. 10, no. 2, Jan. 2020, pp. 1060–76. Scopus, doi:10.1021/acscatal.9b04712.
Journal cover image

Published In

ACS Catalysis

DOI

EISSN

2155-5435

Publication Date

January 17, 2020

Volume

10

Issue

2

Start / End Page

1060 / 1076

Related Subject Headings

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