4.8 Article

Enantioselective Synthesis of Polysubstituted Cyclopentanones by Organocatalytic Double Michael Addition Reactions

Journal

ORGANIC LETTERS
Volume 12, Issue 16, Pages 3634-3637

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol101414b

Keywords

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Funding

  1. Ministry of Science and Technology [2009ZX09501-00]
  2. Chinese Academy of Sciences
  3. National Natural Science Foundation of China [20632050, 20921091]

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The O-TMS-protected diphenylprolinol-catalyzed cascade double Michael addition reactions of alpha,beta-unsaturated aldehydes with a beta-keto ester bearing a highly electron-deficient olefin unit occur smoothly to afford polysubstituted cyclopentanones. This process allows formation of four contiguous stereocenters in the cyclopentanone ring in one-step with excellent enantioselectivity.

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