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Mechanistic study of the Mitsunobu reaction
Chuljin Ahn1, Reuben Correia, Philip DeShong
1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
The Journal of Organic Chemistry
|March 16, 2002
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.