4.8 Article

Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 48, Pages 16748-16751

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja509919x

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Funding

  1. National Research Foundation Singapore [NRF-RF-2009-05]
  2. Nanyang Technological University
  3. JST, CREST

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Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.

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