561276-74-2Relevant academic research and scientific papers
New insights into the reduction of β,δ-diketo-sulfoxides
Hanquet, Gilles,Salom-Roig, Xavier J.,Gressot-Kempf, Laurence,Lanners, Steve,Solladie, Guy
, p. 1291 - 1301 (2003)
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 occurring during the reduction of unprotected β,δ-diketo-sulfoxides and showed that judicious protection of the δ-carbonyl group gave all diastereoisomers of β-hydroxy-δ-ketosulfoxides.
