New Domino Reactions with Sultones

Ashraf M. Mohamed Ewas; Kamal M. Dawood; Katrin Spinde; Yuzhou Wang; Anne Jäger; Peter Metz

doi:10.1055/s-0029-1217371

LETTER

New Domino Reactions with Sultones

Ashraf M. Mohamed Ewas^a,b, Kamal M. Dawood^a,c, Katrin Spinde^a, Yuzhou Wang^a, Anne Jäger^a, Peter Metz*^a
^a Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstraße 66,01069 Dresden, Germany
Fax: +49(351)46333162; e-Mail: peter.metz@chemie.tu-dresden.de;
^b Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo 12622, Egypt
^c Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Abstract

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Abstract

Hydroxyl-containing α,β-unsaturated δ-sultones undergo a diastereoselective conjugate reduction by Red-Al. This transformation can be extended to a domino elimination/1,4-hydride addition of a tricyclic sultone substrate that is readily available via intramolecular Diels-Alder reaction. Bicyclic γ-keto δ-sultones are converted into diastereomerically pure oxabicyclic ketones in a domino desulfurization/oxy-Michael addition using DBU.

Key words

sultones - conjugate additions - reductions - desulfurizations - domino reactions

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References

References and Notes

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