Darzens Condensation (Darzens-Claisen Reaction, Glycidic Ester Condensation)

G. Darzens, Compt. Rend. 139, 1214 (1904); 141, 766 (1905); 142, 214 (1906).

Formation of α,β-epoxy esters (glycidic esters) by the condensation of aldehydes or ketones with esters of α-haloacids; the corresponding thermally unstable glycidic acids yield aldehydes or ketones on decarboxylation:



M. S. Newman, B. J. Magerlein, Org. React. 5, 413 (1949); M. Ballester, Chem. Rev. 55, 283 (1955); H. O. House, Modern Synthetic Reactions (W. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 666-671. Intramolecular reaction: G. Fráter et al., Tetrahedron Letters 34, 2753 (1993). Enantioselectivity: D. Enders, R. Hett, Synlett 1998, 961; S. Arai et al., Tetrahedron 55, 6375 (1999). Modified conditions: R. F. Borch, Tetrahedron Letters 1972, 3761; I. Shibata et al., J. Org. Chem. 57, 6909 (1992). Review: T. Rosen, Comp. Org. Syn. 2, 409-439 (1991).