4.8 Article

Enantioselective Three-Component Kabachnik-Fields Reaction Catalyzed by Chiral Scandium(III)-N,N′-Dioxide Complexes

Journal

ORGANIC LETTERS
Volume 11, Issue 6, Pages 1401-1404

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol9000813

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Funding

  1. National Natural Science Foundation of China [20732003, 20872096]
  2. Ministry of Education [20070610019]

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The N,N'-dioxide-Sc(III) complex has been applied in the three-component Kabachnik-Fields reaction of aldehydes, 2-aminophenol, and diphenyl phosphite, giving the corresponding alpha-amino phosphonates in good yields with high enantioselectivities (up to 87% ee). The direct Kabachnik-Fields reaction proceeded with extremely high reactivity under mild reaction conditions and could be used for large-scale synthesis of the cc-amino phosphonates.

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