X=Y=ZH systems as potential 1,3-dipoles. Part 62: 1,3-Dipolar cycloaddition reactions of metallo-azomethine ylides derived from alpha-iminophosphonates

DÖNDAŞ H. A., Durust Y., Grigg R., Slater M., Sarker M.

TETRAHEDRON, vol.61, no.45, pp.10667-10682, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 61 Issue: 45
  • Publication Date: 2005
  • Doi Number: 10.1016/j.tet.2005.08.079
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.10667-10682
  • Keywords: cycloaddition, iminophosphonate metallo-dipole, azomethine ylide, Y-ZH SYSTEMS, 2-OXOINDOLIN-3-YLIDENE DERIVATIVES, 2-PI COMPONENTS, AMINO ESTERS, IMINES, ACIDS, CATALYSTS, ROUTE
  • Çukurova University Affiliated: No

Abstract

Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et3N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding Michael adduct in some cases. Cycloadditions with the chiral dipolarophile 5R-(1'R,2'S,5'R-menthyloxy)-2-(5H)-furanone (MOF) afforded enantiopure cycloadducts. (c) 2005 Elsevier Ltd. All rights reserved.