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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Published in | Tetrahedron: asymmetry Vol. 14; no. 10; pp. 1291 - 1301 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
16.05.2003
Elsevier |
Subjects | |
Online Access | Get full text |
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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.
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ISSN: | 0957-4166 1362-511X 0957-4166 |
DOI: | 10.1016/S0957-4166(03)00125-3 |