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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

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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.
Journal cover image

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