The Catalyzed Desulfinylative Allylation of Carbonyl Compounds with Alk-2-enesulfonyl Chlorides and Silyl Alk-2-enesulfinates

Authors

  • Chandra M. R. Volla Dr.,

    1. Laboratoire de glycochimie et de synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne (Switzerland), Fax: (+41) 21-693-93-75
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  • Dean Marković Dr.,

    1. Laboratoire de glycochimie et de synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne (Switzerland), Fax: (+41) 21-693-93-75
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  • Sylvain Laclef,

    1. Laboratoire de glycochimie et de synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne (Switzerland), Fax: (+41) 21-693-93-75
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  • Pierre Vogel Prof.

    1. Laboratoire de glycochimie et de synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne (Switzerland), Fax: (+41) 21-693-93-75
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Abstract

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Coupling up with sulfonyl chlorides: An ene reaction of alkenes with SO2⋅BCl3 permits the one-pot conversion of simple alkenes into β,γ-unsaturated sulfonyl chlorides or sulfinic silyl esters. These compounds can then be used as nucleophilic allylating agents with aldehydes and ketones to generate the corresponding homoallylic alcohols (see scheme) with good chemo- and diastereoselectivity in the presence of a suitable catalyst and reducing agent.

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