Synthesis of a new enantiomerically pure P-chiral phosphine and its use in probing the mechanism of the Mitsunobu reaction

Takuro Watanabe, Ilya D. Gridnev, Tsuneo Imamoto

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A new enantiomerically pure P-chiral phosphine, (S)-cyclohexylmethyl-(1- naphthyl)phosphine (1) was prepared by phosphine-borane methodology and used in a mechanistic study of the Mitsunobu reaction. Enantiomerically enriched (S)-cyclohexylmethyl(1-naphtyl)phosphine oxide (8) is obtained if the reaction proceeds through the phosphonium salt 4, whereas the intermediate dialkoxyphosphorane 5 leads to racemic phosphine oxide 8. The results of the experiments including the variation of the reaction conditions and the natures of alcohol and carboxylic acid used in the Mitsunobu reaction prove the competition of two alternative mechanisms (reaction via 4 or 5) on the second stage of the Mitsunobu reaction. (C) Wiley-Liss, Inc.

Original languageEnglish
Pages (from-to)346-351
Number of pages6
JournalChirality
Volume12
Issue number5-6
DOIs
Publication statusPublished - 2000 Jan 1
Externally publishedYes

Keywords

  • (S)cyclohexylmethyl (1-naphthyl)phosphine
  • Mitsunobu reaction
  • P-chiral phosphine
  • Phosphine- borane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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