Mechanistic study of the Mitsunobu reaction.
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.
Ahn
Chuljin
C
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Correia
Reuben
R
DeShong
Philip
P
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
D000438:Alcohols; D009943:Organophosphorus Compounds