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Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Publication ,  Journal Article
Shao, X; Li, K; Malcolmson, SJ
Published in: Journal of the American Chemical Society
June 2018

Here we report highly efficient and chemoselective azadiene-imine reductive couplings catalyzed by (Ph-BPE)Cu-H that afford anti-1,2-diamines. In all cases, reactions take place with either aldimine or ketimine electrophiles to deliver a single diastereomer of product in >95:5 er. The products' diamines are easily differentiable, facilitating downstream synthesis.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

June 2018

Volume

140

Issue

23

Start / End Page

7083 / 7087

Related Subject Headings

  • Stereoisomerism
  • Oxidation-Reduction
  • Imines
  • General Chemistry
  • Diamines
  • Copper
  • Catalysis
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Shao, X., Li, K., & Malcolmson, S. J. (2018). Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines. Journal of the American Chemical Society, 140(23), 7083–7087. https://doi.org/10.1021/jacs.8b04750
Shao, Xinxin, Kangnan Li, and Steven J. Malcolmson. “Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.Journal of the American Chemical Society 140, no. 23 (June 2018): 7083–87. https://doi.org/10.1021/jacs.8b04750.
Shao X, Li K, Malcolmson SJ. Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines. Journal of the American Chemical Society. 2018 Jun;140(23):7083–7.
Shao, Xinxin, et al. “Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.Journal of the American Chemical Society, vol. 140, no. 23, June 2018, pp. 7083–87. Epmc, doi:10.1021/jacs.8b04750.
Shao X, Li K, Malcolmson SJ. Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines. Journal of the American Chemical Society. 2018 Jun;140(23):7083–7087.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

June 2018

Volume

140

Issue

23

Start / End Page

7083 / 7087

Related Subject Headings

  • Stereoisomerism
  • Oxidation-Reduction
  • Imines
  • General Chemistry
  • Diamines
  • Copper
  • Catalysis
  • 40 Engineering
  • 34 Chemical sciences
  • 03 Chemical Sciences