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Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
18
Identifiers
DOI: 10.1016/s0040-4039(03)00728-7
Keywords
  • Mitsunobu Reaction
  • Tertiary Alcohols
  • Alkyl Aryl Ether
  • Sn2 Displacement
  • Inversion

Abstract

Abstract Mitsunobu reaction of chiral tertiary alcohol ( S)- 2 with phenol 3 provides the desired ether ( R)- 1 in moderate yields at elevated temperatures (80–100°C). The S N2 displacement pathway is evident by complete inversion of the ( S)-alcohol to ( R)-ether.

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