Diethylzinc-mediated 1,3-dipolar cycloaddition reaction of chiral azomethine ylides: asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives

Dogan O., Oner I., Ulku D., Arici C.

TETRAHEDRON-ASYMMETRY, cilt.13, sa.19, ss.2099-2104, 2002 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 13 Konu: 19
  • Basım Tarihi: 2002
  • Doi Numarası: 10.1016/s0957-4166(02)00576-1
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Sayfa Sayıları: ss.2099-2104

Özet

Asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives was successfully achieved by diethylzinc-mediated 1,3-dipolar cycloaddition reactions of chiral azomethine ylides with a number of electron-deficient dipolarophiles. Chiral azomethine ylides were formed by condensing glycyl sultam with ferrocenecarboxaldehyde via imine tautomerization and complexation with diethylzinc. All of the cycloaddition reactions gave ferrocenyl-substituted pyrrolidine derivatives with very high regio- and diastereoselectivity in reasonable yields. (C) 2002 Elsevier Science Ltd. All rights reserved.