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Highly efficient chiral resolution and determination of absolute configuration of 2-alkanols by using a cyclopenta[b]furan derivative

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
8
Identifiers
DOI: 10.1016/j.tetlet.2003.12.104
Keywords
  • Chiral Resolution
  • Acetal
  • Thin Layer Chromatography
  • Alkenyl Ether
Disciplines
  • Chemistry

Abstract

Abstract The reaction of 3a-benzhydryl-3,3a,4,5-tetrahydro-2 H-cyclopenta[ b]furan and various 2-alkanols in the presence of a catalytic amount of pyridinium 4-tolunesulfonate in dichloromethane gave 3a-benzhydryl-6a-(1-methyl-aloxy)-hexahydrocyclopenta[ b]furan in more than 90% chemical yields. The resulting diastereomeric mixture is easily separable on silica gel chromatography because of the large Δ R f value (briefly 0.1). Absolute configuration of the 2-alkanols can be easily estimated by the chemical shifts of 1H and 13C NMR of methyne group of the benzhydryl moiety.

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