Benkeser Reduction

R. A. Benkeser et al., J. Am. Chem. Soc. 74, 5699 (1952); 77, 3230 (1955).

Reduction of aromatic and olefinic compounds with lithium or calcium and low molecular weight amines to monounsaturated olefins, as well as the fully reduced products. The extent of reduction and selectivity can be controlled by varying the reaction conditions:

Selectivity study: R. A. Benkeser et al., Tetrahedron Letters no. 16, 1 (1960). Comparative review: E. M. Kaiser, Synthesis 1972, 391-415 passim. Scope and limitations: R. A. Benkeser et al., J. Org. Chem. 48, 2796 (1983). Synthetic applications: C. Eaborn et al., J. Chem. Soc. Perkin Trans. I 1975, 475; R. Eckrich, D. Kuck, Synlett 1993, 344. Cf. Birch Reduction.