Intramolecular displacement of phenylselenone by a hydroxy group: stereoselective synthesis of 2-substituted tetrahydrofurans

Org Lett. 2013 Aug 2;15(15):3906-9. doi: 10.1021/ol401653w. Epub 2013 Jul 19.

Abstract

An efficient and stereocontrolled synthesis of 2-substituted tetrahydrofurans has been achieved. The approach employs the asymmetric reduction of γ-phenylseleno ketones obtained by three different procedures that are peculiarly applied to the synthesis of such compounds. Finally, the intramolecular substitution of the phenylselenone residue by the oxygen atom of a hydroxy group gives the tetrahydrofuran ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry*
  • Molecular Structure
  • Selenium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Furans
  • Selenium Compounds