Reformatsky (Reformatskii) Reaction

S. Reformatskii, Ber. 20, 1210 (1887); J. Russ. Phys. Chem. Soc. 22, 44 (1890).

Condensation of aldehydes or ketones with organozinc derivatives of α-halo esters to yield β-hydroxy esters:



Early reviews: R. L. Shriner, Org. React. 1, 1 (1942); H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 671-682; M. W. Rathke, Org. React. 22, 423 (1975). Use of thiocarbonyl electrophiles: M. Chandrasekharam et al., Tetrahedron Letters 34, 6439 (1993). Application to the synthesis of β-keto esters: C. Kashima et al., J. Org. Chem. 58, 793 (1993). Asymmetric synthesis: D. Pini et al., Tetrahedron Asymmetry 5, 1875 (1994). Methods development for the synthesis of β-lactones: H. Schick et al., Tetrahedron 51, 2939 (1995). Reviews: A. Fürstner, Synthesis 1989, 571-590; M. W. Rathke, P. Weipert, Comp. Org. Syn. 2, 277-299 (1991). Cf. Aldol Reaction; Blaise Reaction.