Highly diastereoselective synthesis of trans-2,5-disubstituted tetrahydrofurans

J Org Chem. 2004 Apr 30;69(9):3240-1. doi: 10.1021/jo035811a.

Abstract

trans-2,5-Disubstituted tetrahydrofurans were obtained as major diastereomers (trans/cis ratio 90:10-100:0) when acetylated gamma-lactols derived from (S)-glutamic acid were treated with titanium enolates of N-acetyl (R)-oxazolidin-2-thiones. A simple transesterification allowed us to obtain the corresponding methyl esters and recover the chiral auxiliary.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Esterification
  • Furans / chemical synthesis*
  • Glutamic Acid / chemistry
  • Lactones / chemistry
  • Organometallic Compounds / chemistry
  • Oxazolidinones / chemistry
  • Stereoisomerism
  • Titanium / chemistry

Substances

  • Furans
  • Lactones
  • Organometallic Compounds
  • Oxazolidinones
  • Glutamic Acid
  • Titanium