Highly selective intermolecular one-pot three component 1,3-dipolar cycloaddition reaction of aldehydes, with phosphonates and proline

Subasi N. T., Yalcinkaya H., DEMİR A. G.

TETRAHEDRON, vol.73, no.30, pp.4329-4334, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 73 Issue: 30
  • Publication Date: 2017
  • Doi Number: 10.1016/j.tet.2017.05.091
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4329-4334
  • Keywords: Dipolar cycloaddition, Proline, Acylphosphonate, Azomethine ylide, ASYMMETRIC ALDOL REACTIONS, ACYL ANION EQUIVALENTS, AZOMETHINE YLIDES, ACYLPHOSPHONATES, ORGANOCATALYSIS, GENERATION
  • Middle East Technical University Affiliated: Yes

Abstract

The use of L-proline to act as an organocatalyst in the aldol reaction of acylphosphonates and non enolizable aldehydes failed; however, it reacted with the aldehydes to afford azomethine ylides after decarboxylation that in turn underwent 1,3-dipolar cycloaddition with the acylphosphonates to form a bicyclic hexahydropyrrolo[1,2-c]oxazol-1-ylphosphonates in good yield. No azomethine ylide formation was observed on the reaction of acylphosphonates with proline. (C) 2017 Elsevier Ltd. All rights reserved.