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

研究成果: Article査読

37 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)346-351
ページ数6
ジャーナルChirality
12
5-6
DOI
出版ステータスPublished - 2000 1月 1
外部発表はい

ASJC Scopus subject areas

  • 分析化学
  • 触媒
  • 薬理学
  • 創薬
  • 分光学
  • 有機化学

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