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

✍ Scribed by Gilles Hanquet; Xavier J. Salom-Roig; Laurence Gressot-Kempf; Steve Lanners; Guy Solladié

Book ID: 104359728
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 429 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00125-3

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✦ Synopsis

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.

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