Facile assembly of chiral tetrahydrothiopyrans containing four consecutive stereocenters via an organocatalytic enantioselective Michael-Michael cascade

Org Lett. 2014 Feb 7;16(3):692-5. doi: 10.1021/ol4033557. Epub 2014 Jan 17.

Abstract

An organocatalytic enantioselective Michael-Michael cascade reaction has been implemented for the creation of structurally variant chiral tetrahydrothiopyrans. The process is realized by employment of new bifunctional ketothioether enones and proceeds highly enantioselectively with formation of four consecutive stereogenic centers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry*
  • Sulfides / chemistry*

Substances

  • Pyrans
  • Sulfhydryl Compounds
  • Sulfides
  • thiopyran