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)
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.
see article for more examples
alcohols, substitution, Mitsunobu reaction, phosphorus