Enantioselective synthesis of polysubstituted cyclopentanones by organocatalytic double Michael addition reactions.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
- Published Article
American Chemical Society
- Publication Date
Aug 20, 2010
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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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/20704408