2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.
Publication
, Journal Article
Malcolmson, SJ; Li, K; Shao, X
Published in: Synlett : accounts and rapid communications in synthetic organic chemistry
July 2019
The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.
Duke Scholars
Published In
Synlett : accounts and rapid communications in synthetic organic chemistry
DOI
ISSN
0936-5214
Publication Date
July 2019
Volume
30
Issue
11
Start / End Page
1253 / 1268
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Malcolmson, S. J., Li, K., & Shao, X. (2019). 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines. Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry, 30(11), 1253–1268. https://doi.org/10.1055/s-0037-1611770
Malcolmson, Steven J., Kangnan Li, and Xinxin Shao. “2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.” Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry 30, no. 11 (July 2019): 1253–68. https://doi.org/10.1055/s-0037-1611770.
Malcolmson SJ, Li K, Shao X. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines. Synlett : accounts and rapid communications in synthetic organic chemistry. 2019 Jul;30(11):1253–68.
Malcolmson, Steven J., et al. “2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.” Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry, vol. 30, no. 11, July 2019, pp. 1253–68. Epmc, doi:10.1055/s-0037-1611770.
Malcolmson SJ, Li K, Shao X. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines. Synlett : accounts and rapid communications in synthetic organic chemistry. 2019 Jul;30(11):1253–1268.
Published In
Synlett : accounts and rapid communications in synthetic organic chemistry
DOI
ISSN
0936-5214
Publication Date
July 2019
Volume
30
Issue
11
Start / End Page
1253 / 1268
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry