Payne Rearrangement

G. B. Payne, J. Org. Chem. 27, 3819 (1962).

Base-promoted isomerization of 2,3-epoxyalcohols. Configuration at C-2 is inverted:



In conjunction with nucleophilic ring opening: T. Katsuki et al., ibid. 47, 1373 (1982); C. H. Behrens et al., ibid. 50, 5687 (1985); P. C. B. Page et al., J. Chem. Soc. Perkin Trans. I 1990, 1375; T. Konosu et al., Chem. Pharm. Bull. 40, 562 (1992). Aza-Payne rearrangements: T. Ibuka et al., J. Org. Chem. 60, 2044 (1995); K. Nakai et al., Tetrahedron Letters 36, 6247 (1995). Enhanced stereoselectivity: W. C. Frank, Tetrahedron Asymmetry 9, 3745 (1998). Review of aza-Payne: T. Ibuka et al., Chem. Soc. Rev. 27, 145-154 (1998).