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Synlett 1995; 1995(12): 1264-1266
DOI: 10.1055/s-1995-5242
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Synthesis and Diels-Alder Reactions of Semicyclic Sugar Containing Dienes

Ali Abas, Roy L. Beddoes, Jeremy C. Conway, Peter Quayle* , Christopher J. Urch
  • *Department of Chemistry, The Victoria University of Manchester, Manchester M13 9PL, UK
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Publication Date:
31 December 2000 (online)

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Semicyclic pyranose-derived dienes are readily available via Stille coupling of the corresponding 2-(tri-n-butylstannyl)glucal with a variety of vinyl halides. Diels-Alder reactions of the derived dienes with Cookson’s reagent exhibit good levels of facial selectivity.

Diene - Diels-Alder - Glucal - Stille - Palladium

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