4.8 Article

Catalytic enantioselective reformatsky reaction with ortho-substituted diarylketones

Journal

ORGANIC LETTERS
Volume 10, Issue 18, Pages 4041-4044

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801574m

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Funding

  1. Dutch Ministry of Economic Affairs
  2. Spanish Ministry of Education and Science

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The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me2Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

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