Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

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Abstract

The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number21
Early online date23 Jun 2016
DOIs
Publication statusPublished - Jul 2016

Keywords

  • Organocatalysis
  • Enantioselective catalysis
  • Oxygen heterocycles

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