title: Mechanistic study of the Mitsunobu reaction.
abstract: The Mitsunobu reaction occurs typically with inversion of configuration in secondary alcohol derivatives. In this paper, a mechanistic explanation for lactonizations of hindered alcohols under Mitsunobu conditions with retention is proposed. This involves the intermediacy of an acyloxyphosphonium salt followed by acyl transfer to the alcohol.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
authors.forename: Chuljin
authors.initials: C
authors.lastname: Ahn
authors.forename: Reuben
authors.initials: R
authors.lastname: Correia
authors.forename: Philip
authors.initials: P
authors.lastname: DeShong
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D009943:Organophosphorus Compounds