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

Date

2002-10-01

Author

Doğan, Özdemir
ÖNER, İmdat
DİNÇER, Ülkü
ARICI, Cengiz

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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.

Subject Keywords

Tricyclic Core, 2-Amino Esters, Auxiliary, Construction, Generation, Sarain

URI

https://hdl.handle.net/11511/40335

Journal

Tetrahedron-Asymmetry

DOI

https://doi.org/10.1016/s0957-4166(02)00576-1

Collections

Department of Chemistry, Article

Citation Formats

Ö. Doğan, İ. ÖNER, Ü. DİNÇER, and C. ARICI, “Diethylzinc mediated 1 3 dipolar cycloaddition reaction of chiral azomethine ylides asymmetric synthesis of ferrocenyl substituted pyrrolidine derivatives,” Tetrahedron-Asymmetry, vol. 13, pp. 2099–2104, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40335.