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Synlett 2009(11): 1773-1776  
DOI: 10.1055/s-0029-1217371
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

New Domino Reactions with Sultones

Ashraf M. Mohamed Ewasa,b, Kamal M. Dawooda,c, Katrin Spindea, Yuzhou Wanga, Anne Jägera, 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
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Publication History

Received 31 March 2009
Publication Date:
12 June 2009 (online)

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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

    References and Notes

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8

MeLi is superior to BuLi for elimination of 5a to yield 6a.³

11

The ratio of the diastereomers 7a/8a varied to some extent from run to run, while 7b was usually obtained as a single isomer.

12

CCDC 724219 contains the supplementary X-ray crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystall-ographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.