Hetero Diels-Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates

Polat-Cakir S., DEMİR A. G.

TETRAHEDRON, vol.67, no.13, pp.2396-2401, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 13
  • Publication Date: 2011
  • Doi Number: 10.1016/j.tet.2011.02.007
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2396-2401
  • Keywords: Acyl phosphonates, Hereto Diels-Alder, Glycosyl phosphonates, ANION EQUIVALENTS, ACYLPHOSPHONATES, GLYCOSIDATION, CATALYSIS, KETONES
  • Middle East Technical University Affiliated: Yes

Abstract

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.