
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
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MLA
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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.

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