4.8 Article

Sc(OTf)3-Catalyzed Conjugate Allylation of Alkylidene Meldrum's Acids

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ORGANIC LETTERS
卷 11, 期 9, 页码 1919-1922

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AMER CHEMICAL SOC
DOI: 10.1021/ol9003959

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  1. Merck Frosst Center for Therapeutic Research
  2. Natural Sciences and Engineering Research Council of Canada (NSERC)
  3. Canadian Foundation for Innovation
  4. Ontario Innovation Trust
  5. University of Waterloo
  6. Government of Canada for a graduate scholarship (NSERC CGS-D)

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Alkylidene Meldrum's acids are allylated in a conjugate fashion by allyltin nucleophiles under mild Sc(OTf)(3)-catalyzed conditions. The addition is functional group tolerant and reactions with nonracemic alkylidenes are highly diastereoselective. Allylation of alkylidenes derived from alpha-ketoesters yield all-carbon quaternary stereocenters.

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