Diastereo- and enantioselective construction of cyclohexanone-fused spirospyrazolones containing four consecutive stereocenters through asymmetric sequential reactions

Jun Hua Li, Zhi Hao Cui, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

The diastereo- and enantioselective synthesis of cyclohexanone-fused spirospyrazolones containing four consecutive chiral centers has been successfully developed through an asymmetric Michael/Michael/aldol cascade reaction catalyzed by the combination of a bifunctional squaramide and diphenylprolinol silyl ether, followed by a sequential oxidation with pyridinium chlorochromate. This protocol affords cyclohexanone-fused spirospyrazolones in moderate to high yields, moderate to good diastereoselectivities and perfect enantioselectivities.

Original languageEnglish
Pages (from-to)1087-1090
Number of pages4
JournalOrganic Chemistry Frontiers
Volume3
Issue number9
DOIs
Publication statusPublished - Sept 2016

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Li, J. H., Cui, Z. H., & Du, D. M. (2016). Diastereo- and enantioselective construction of cyclohexanone-fused spirospyrazolones containing four consecutive stereocenters through asymmetric sequential reactions. Organic Chemistry Frontiers, 3(9), 1087-1090. https://doi.org/10.1039/c6qo00208k