4.8 Article

Ru-Catalyzed Asymmetric Hydrogenative/Transfer Hydrogenative Desymmetrization of Meso-Epoxy Diketones

Journal

ORGANIC LETTERS
Volume 18, Issue 11, Pages 2640-2643

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01073

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Funding

  1. National Natural Science Foundation of China [21232004, 21472123, 21572131]
  2. Science and Technology Commission of Shanghai Municipality [14XD1402300]
  3. China Postdoctoral Science Foundation [2014M551397]

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Via a strategy of asymmetric reductive desymmetrization, chiral cis-epoxy naphthoquinols with multiple contiguous stereocenters and functional groups Were synthesized with excellent enantioselectivities (96-99% ee) and diastereoselectivities (8/1-15/1). A combined asymmetric hydrogenation/transfer hydrogenation mechanism was proposed based on experimental results.

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