4.8 Article

Lewis-Acid-Catalyzed Asymmetric Alkynylation of Alkynyl 1,2-Diketones: Controllable Formation of 3(2H)-Furanones and α-Hydroxy Ketones

Journal

ORGANIC LETTERS
Volume 22, Issue 17, Pages 6948-6953

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02505

Keywords

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Funding

  1. National Natural Science Foundation of China [21871260, 21502192]
  2. Chinese Academy of Sciences [XDB20000000]
  3. Fujian Natural Science Foundation [2018J05035]
  4. China Postdoctoral Science Foundation [2018M630734]

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We report the highly regio- and enantioselective alkynylation of alkynyl 1,2-diketones under Lewis acid catalysis, leading to the formation of a series of biologically important 3(2H)-furanones with high to excellent ee values. Moreover, a slight change of the reaction conditions produces a range of highly functionalized alpha-hydroxy ketones with a high level of enantioselectivity. A variety of further transformations can be easily achieved, demonstrating the synthetic potential of this protocol.

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