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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*

*Graduate School of Material Science, University of Hyogo, 3-2-1, Kohto, Kamigori, Hyogo 678-1297, Japan, Email: sugimurasci.u-hyogo.ac.jp

N. Muramoto, K. Yoshino, T. Misaki, T. Sugimura, Synthesis, 2013, 45, 931-935.

DOI: 10.1055/s-0032-1318329 (free Supporting Information)


Abstract

4-(Diphenylphosphino)benzoic acts both a as reductant and a pronucleophile in Mitsunobu reactions. 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, followed by simple basic extraction, to give an inverted secondary alcohol in sufficient stereo and chemical purities.

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Key Words

alcohols, substitution, Mitsunobu reaction, phosphorus


ID: J66-Y2013-0810