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, cilt.61, sa.45, ss.10667-10682, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 45
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.08.079
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.10667-10682
  • Anahtar Kelimeler: cycloaddition, iminophosphonate metallo-dipole, azomethine ylide, Y-ZH SYSTEMS, 2-OXOINDOLIN-3-YLIDENE DERIVATIVES, 2-PI COMPONENTS, AMINO ESTERS, IMINES, ACIDS, CATALYSTS, ROUTE
  • Çukurova Üniversitesi Adresli: Hayır

Özet

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.