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, vol.13, no.19, pp.2099-2104, 2002 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 13 Issue: 19
  • Publication Date: 2002
  • Doi Number: 10.1016/s0957-4166(02)00576-1
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2099-2104

Abstract

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.