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

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 hypothes...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 14; no. 10; pp. 1291 - 1301
Main Authors Hanquet, Gilles, Salom-Roig, Xavier J., Gressot-Kempf, Laurence, Lanners, Steve, Solladié, Guy
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.05.2003
Elsevier
Subjects
Chemical Sciences
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Organic chemistry
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ACID
ENANTIOSELECTIVE SYNTHESIS
BETA-HYDROXYKETONES
BETA,DELTA-DIKETOSULFOXIDES
1,3-DIOLS
CHIRAL SULFOXIDES
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Summary: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. Graphic
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/S0957-4166(03)00125-3