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Enantioselective synthesis of polysubstituted cyclopentanones by organocatalytic double Michael addition reactions.

Authors
  • Ma, Anqi1
  • Ma, Dawei
  • 1 State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. , (China)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Aug 20, 2010
Volume
12
Issue
16
Pages
3634–3637
Identifiers
DOI: 10.1021/ol101414b
PMID: 20704408
Source
Medline
License
Unknown

Abstract

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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