4.8 Article

Direct Catalytic Enantioselective Benzylation from Aryl Acetic Acids

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 50, Pages 17418-17422

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b11390

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Funding

  1. NSERC Canada
  2. Killam Trusts (IWK fellowship)
  3. Canadian Foundation for Innovation

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We demonstrate that metal-catalyzed enantioselective benzylation reactions of allylic electro-philes can occur directly from aryl acetic acids. The reaction proceeds via a pathway in which decarboxylation is the terminal event, occurring after stereoselective carbon carbon bond formation. This mechanistic feature enables enantioselective benzylation without the generation of a highly basic nucleophile. Thus, the process has broad functional group compatibility that would not be possible employing established protocols.

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