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.
Esterification O 0315 DMEAD: A New Dialkyl Azodicarboxylate for the Mitsunobu Reaction. -The use of DMEAD in the reaction of a variety of alcohols with pronucleophiles results in good yields under sufficient stereospecificity of inversion comparable to the use of DIAD. The isolation of the products is much easier, since the hydrazine produced from DMEAD is highly hydrophilic and completely separable by a simple extraction into neutral water. The hydrazine can be recycled and reused for the synthesis of DMEAD. -(HAGIYA, K.; MURAMOTO, N.; MISAKI, T.; SUGIMURA*, T.; Tetrahedron 65 (2009) 31, 6109-6114; Grad. Sch. Mater. Sci., Univ. Hyogo, Ako, Hyogo 678, Japan; Eng.) -Klein 46-038
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