4.8 Article

Enantioselective Rhodium-Catalyzed Conjugate Alkynylation of 5-Benzylidene Meldrum's Acids with TMS-acetylene

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 41, Pages 14608-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja905336p

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Funding

  1. Government of Ontario
  2. Merck Frosst Center for Therapeutic Research
  3. NSERC
  4. CFI
  5. OIT
  6. University of Waterloo Aaron M. Dumas
  7. University of Waterloo

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The enantiosetective alkynylation of benzylidene Meldrum's acids has been successfully achieved through rhodium-catalyzed addition of TMS-acetylene in the presence of bisphosphine ligand 3,5-Xylyl-MeOBIPHEP. The resulting Meldrum's acids were obtained in good yields and up to 99% enantiomeric excess. The alkynylation method is carried out under mild reactions conditions and is compatible with an array of functional groups.

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