Stereoselective organozinc addition reactions to 1,2-dihydropyrans for the assembly of complex pyran structures

Org Lett. 2002 Jan 24;4(2):293-5. doi: 10.1021/ol010273e.

Abstract

[reaction: see text] Nucleophilic addition of organozincs to 1,2-dihydropyranyl acetates represents a new, broadly defined method for the stereocontrolled synthesis of alpha-substituted pyrans. The products obtained from this process are versatile materials that can be used to construct C-glycosides and other functionalized pyran structures of import. The occurrence of pyranyl groups in both natural products and therapeutically active agents confers added value to the studies described herein.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Organometallic Compounds / chemistry
  • Pyrans / chemical synthesis*
  • Stereoisomerism
  • Zinc / chemistry

Substances

  • Organometallic Compounds
  • Pyrans
  • Zinc