Tetrahedron letters

SmI 2-Induced highly regioselective reduction of α, β-epoxy esters and γ, δ-epoxy-α, β-unsaturated esters. An efficient route to optically active β-hydroxy and δ-hydroxy …

K Otsubo, J Inanaga, M Yamaguchi

Index: Otsubo, Kenji; Inanaga, Junji; Yamaguchi, Masaru Tetrahedron Letters, 1987 , vol. 28, # 38 p. 4437 - 4440

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Citation Number: 92

Abstract

Abstract α, β-Epoxy esters were rapidly reduced at room temperature to yield β-hydroxy esters with retention of the configurations at the β-carbon atoms by using SmI 2-THF-HMPA system in the presence of N, N-dimethylaminoethanol (DMAE). The conditions were successfully applied to the synthesis of vinylogous δ-hydroxy esters.