4.8 Article

Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chirally Modified AZADOs

Journal

ORGANIC LETTERS
Volume 11, Issue 8, Pages 1829-1831

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900441f

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Funding

  1. Japan Society for the Promotion of Science [17390002]
  2. Ministry of Education, Culture, Sports, Science, and Technology, Japan [19790005]
  3. Uehara Memorial Fundation for the Promotion of Life Science
  4. Grants-in-Aid for Scientific Research [19790005, 21390001, 17390002] Funding Source: KAKEN

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A highly enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols has been accomplished using asymmetric organocatalysis. A panel of chirally modified 2-azaadamantane N-oxyls (AZADOs) exhibit superior catalytic activity and high enantioselectivity, allowing us to obtain optically active secondary alcohols with a k(rel) value up to 82.2.

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