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2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

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

We introduce a new strategy for synthesis of chiral amines: couplings of α-aminoalkyl nucleophiles generated by enantioselective migratory insertion of 2-azadienes to a Cu-H. In this report, we demonstrate its application in catalytic reductive coupling of 2-azadienes and ketones to furnish 1,2-amino tertiary alcohols with vicinal stereogenic centers.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

January 2018

Volume

140

Issue

2

Start / End Page

598 / 601

Related Subject Headings

  • Stereoisomerism
  • Polyenes
  • Oxidation-Reduction
  • Molecular Structure
  • Ketones
  • General Chemistry
  • Copper
  • Catalysis
  • Aza Compounds
  • Amines
 

Citation

APA
Chicago
ICMJE
MLA
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Li, K., Shao, X., Tseng, L., & Malcolmson, S. J. (2018). 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones. Journal of the American Chemical Society, 140(2), 598–601. https://doi.org/10.1021/jacs.7b12213
Li, Kangnan, Xinxin Shao, Luke Tseng, and Steven J. Malcolmson. “2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.Journal of the American Chemical Society 140, no. 2 (January 2018): 598–601. https://doi.org/10.1021/jacs.7b12213.
Li K, Shao X, Tseng L, Malcolmson SJ. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones. Journal of the American Chemical Society. 2018 Jan;140(2):598–601.
Li, Kangnan, et al. “2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.Journal of the American Chemical Society, vol. 140, no. 2, Jan. 2018, pp. 598–601. Epmc, doi:10.1021/jacs.7b12213.
Li K, Shao X, Tseng L, Malcolmson SJ. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones. Journal of the American Chemical Society. 2018 Jan;140(2):598–601.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

January 2018

Volume

140

Issue

2

Start / End Page

598 / 601

Related Subject Headings

  • Stereoisomerism
  • Polyenes
  • Oxidation-Reduction
  • Molecular Structure
  • Ketones
  • General Chemistry
  • Copper
  • Catalysis
  • Aza Compounds
  • Amines