4.5 Article

Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 17, Pages 3570-3574

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402199

Keywords

Oxygen heterocycles; Michael addition; Lewis acids; Domino reactions; Nucleophilic addition

Funding

  1. Council of Scientific and Industrial Research (CSIR), New Delhi
  2. Department of Science and Technology (DST), New Delhi
  3. CSIR

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A Lewis acid catalyzed tandem nucleophilic addition/oxa-Michael reaction was developed for the synthesis of cis-2,6-disubstituted tetrahydropyran (THP) derivatives in good yields with excellent diastereoselectivities. The strategy was successfully used in the construction of THP derivatives with three stereocenters in a highly stereoselective fashion.

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