Wharton Reaction

P. S. Wharton, D. H. Bohlen, J. Org. Chem. 26, 3615 (1961); P. S. Wharton, ibid. 4781.

Reduction of α,β-epoxy ketones by hydrazine to allylic alcohols:



Improved procedure: C. Dupuy, J. L. Luche, Tetrahedron 45, 3437 (1989). Synthetic applications: S. Takano et al., Synlett 1991, 636; T. Yoshimitsu et al., Synthesis 1994, 1029; K. Yamada et al., J. Org. Chem. 63, 3666 (1998). Review: D. Caine, Org. Prep. Proced. Int. 20, 3-8 (1988); A. R. Chamberlin, D. J. Sall, Comp. Org. Syn. 8, 927-929 (1991). Cf. Eschenmoser Fragmentation; Grob Fragmentation.