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

2002-10-01
Doğan, Özdemir
ÖNER, İmdat
DİNÇER, Ülkü
ARICI, Cengiz
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.