4.8 Article

Enantioselective Oxidative Ring-Opening Reaction of Aziridines with α-Nitroesters Using Cinchona Alkaloid Amide/Nickel(II) Catalysts

Journal

ORGANIC LETTERS
Volume 19, Issue 1, Pages 74-77

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03346

Keywords

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Funding

  1. MEXT [26105727]
  2. Uehara Memorial Foundation
  3. Grants-in-Aid for Scientific Research [15H00874, 26410117, 16K05720, 16J06021] Funding Source: KAKEN

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The enantioselective oxidative ring-opening reaction of aziridines with alpha-nitroacetates has been developed. Good yields and enantioselectivity were observed for the reaction of various aziridines using a novel cinchona alkaloid amide/NiBr2 catalyst. Both enantiomers of products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of alpha-aminoketones.

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