New insights into the reduction of β, δ-diketo-sulfoxides

G Hanquet, XJ Salom-Roig, L Gressot-Kempf…

Index: Hanquet, Gilles; Salom-Roig, Xavier J.; Gressot-Kempf, Laurence; Lanners, Steve; Solladie, Guy Tetrahedron Asymmetry, 2003 , vol. 14, # 10 p. 1291 - 1301

Full Text: HTML

Citation Number: 8

Abstract

New developments in the reduction of β, δ-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the β-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the δ-position) as the major one. We propose a rationale to explain the side reactions ...