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Article Dans Une Revue Tetrahedron: Asymmetry Année : 2003

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

Résumé

New developments in the reduction of b,d-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the b-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the d-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected b,d-diketo-sulfoxides and showed that judicious protection of the d-carbonyl group gave all diastereoisomers of b-hydroxy-d-ketosulfoxides.

Domaines

Chimie organique

Dates et versions

hal-03468396 , version 1 (08-12-2021)

Identifiants

Citer

Gilles Hanquet, Xavier J Salom-Roig, Laurence Gressot-Kempf, Steve Lanners, Guy Solladié. New insights into the reduction of β,δ-diketo-sulfoxides. Tetrahedron: Asymmetry, 2003, 14 (10), pp.1291-1301. ⟨10.1016/S0957-4166(03)00125-3⟩. ⟨hal-03468396⟩
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