Published January 1, 2011 | Version v1
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Hetero Diels-Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates

  • 1. Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

Description

We have prepared glycosyl type phosphonates via hetero Diels-Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky's diene required thermal activation to yield the desired dihydropyranones in good yield (70-91%). The reactions with Brassard's diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33-69%). (C) 2011 Elsevier Ltd. All rights reserved.

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