4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 2, Pages 598-601

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b12213

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Funding

  1. Duke University
  2. Duke Chemistry Department
  3. ACS Petroleum Research Fund [56575-DNI1]
  4. NIH [GM124286]

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We introduce a new strategy for synthesis of chiral amines: couplings of alpha-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.

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