An Enantioselective Synthesis of Substituted Cyclohexanone Derivatives with an All-Carbon Quaternary Stereocenter by Using an Organocatalytic Asymmetric Domino Double Michael Addition

Chi Han Chen, Chi Ting Ko, Ganapuram Madhusudhan Reddy, Chia Jui Lee, Wenwei Lin

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5 Citations (Scopus)

Abstract

A cinchona alkaloid-catalyzed enantioselective method has been developed for the synthesis of densely functionalized cyclohexanone derivatives with excellent diastereoselectivities and good enantioselectivities [diastereomeric ratio (dr) >95:5 and an enantiomeric excess (ee) value up to 86%]. The products have an all-carbon quaternary center that contains both a cyano and ester group flanked by two vicinal tertiary stereocenters. By using a one-pot procedure, the tautomeric products were then transformed into the corresponding pyrazoles, which were obtained as single isomers in good yields. A quinine-catalyzed enantioselective method has been reported to generate polysubstituted cyclohexenes that have an all-carbon quaternary center. The resulting isomeric product mixtures were easily converted into the corresponding pyrazoles through a one-pot procedure.

Original languageEnglish
Pages (from-to)5254-5265
Number of pages12
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number23
DOIs
Publication statusPublished - 2015 Aug 1

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Keywords

  • Asymmetric synthesis
  • Carbocycles
  • Domino reactions
  • Enones
  • Michael addition
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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