Mitsunobu Reaction with 4-(Diphenylphosphino)benzoic Acid: A Separation-Friendly Bifunctional Reagent that Serves as Both a Reductant and a Pronucleophile

Natsuko Muramoto; Kazuki Yoshino; Tomonori Misaki; Takashi Sugimura

doi:10.1055/s-0032-1318327

Synthesis, Table of Contents

Synthesis 2013; 45(7): 931-935
DOI: 10.1055/s-0032-1318327

paper

Mitsunobu Reaction with 4-(Diphenylphosphino)benzoic Acid: A Separation-Friendly Bifunctional Reagent that Serves as Both a Reductant and a Pronucleophile

Authors

Natsuko Muramoto

Graduate School of Material Science, University of Hyogo, 3-2-1, Kohto, Kamigori, Hyogo 678-1297, Japan Fax: +81(791)580115 Email: sugimura@sci.u-hyogo.ac.jp
Kazuki Yoshino

Graduate School of Material Science, University of Hyogo, 3-2-1, Kohto, Kamigori, Hyogo 678-1297, Japan Fax: +81(791)580115 Email: sugimura@sci.u-hyogo.ac.jp
Tomonori Misaki

Graduate School of Material Science, University of Hyogo, 3-2-1, Kohto, Kamigori, Hyogo 678-1297, Japan Fax: +81(791)580115 Email: sugimura@sci.u-hyogo.ac.jp
Takashi Sugimura*

Graduate School of Material Science, University of Hyogo, 3-2-1, Kohto, Kamigori, Hyogo 678-1297, Japan Fax: +81(791)580115 Email: sugimura@sci.u-hyogo.ac.jp

Abstract

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Abstract

4-(Diphenylphosphino)benzoic acid was used for the Mitsunobu reaction as a bifunctional reagent that served as both a reductant and a pronucleophile. When combined with di-2-methoxyethyl azodicarboxylate, inversion of a secondary alcohol stereospecifically occurred to give an ester carrying a phosphine oxide group. The reaction mixture was directly hydrolyzed to give an inverted secondary alcohol in sufficient stereo and chemical purities by the presently developed chromatography-free process in conjunction with basic extraction, drying, and concentration.

Key words

alcohols - substitution - Mitsunobu reaction - phosphorus

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References

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Supplementary Material

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