Diethylzinc-mediated 1,3-dipolar cycloaddition reaction of chiral azomethine ylides: asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives
TETRAHEDRON-ASYMMETRY, cilt.13, sa.19, ss.2099-2104, 2002 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 13 Sayı: 19
- Basım Tarihi: 2002
- Doi Numarası: 10.1016/s0957-4166(02)00576-1
- Dergi Adı: TETRAHEDRON-ASYMMETRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2099-2104
- Hacettepe Üniversitesi Adresli: Hayır
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.