4.8 Article

Catalytic Enantioselective Epoxidation of Tertiary Allylic and Homoallylic Alcohols

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 9, Pages 3411-3413

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja401182a

Keywords

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Funding

  1. National Institutes of Health [2R01GM068433]
  2. CONACYT (Mexico) [184749]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [1048528] Funding Source: National Science Foundation
  5. Grants-in-Aid for Scientific Research [23225002] Funding Source: KAKEN

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An efficient and versatile method for the enantioselective epoxidation of both tertiary allylic and homoallylic alcohols catalyzed by Hf(IV)-bishydroxamic acid (BHA) complexes is described. Asymmetric epoxidation, kinetic resolution, and desymmetrization have been developed, demonstrating the flexible nature of the Hf(IV)-BHA system. This is the first report in which these substrates were obtained with enantioselectivities of up to 99%.

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