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
DİNÇER, Ülkü
ARICI, Cengiz

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

30
views

0
downloads

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

Suggestions

OpenMETU
Core

Lewis acid catalyzed 1,3-dipolar cycloadditon reactions of stabilized azomethine ylides Doğan, Özdemir; KANIŞKAN, Ümit (2001-01-01) Diethylzinc was tested for the first time as the Lewis acid in 1,3-dipolar cycloaddition reactions of azomethine ylides to synthesize pyrrolidine derivatives. A new, easily applicable and highly selective method was developed for the synthesis of highly substituted pyrrolidines. By the application of this method, the synthesis of three new pyrrolidine derivatives was achieved.
Asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohol derivatives and applications in various asymmetric transformation reactions Odabaş, Serhat; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of N-aryl substituted chiral 1,4-aminoalcohols and their applications in asymmetric borane reduction and enantioselective diethylzinc addition to benzaldehyde reactions were performed starting from meso-anhydride 51 that is the cycloadduct of cyclopentadiene and maleic anhydride. The desymmetrization of meso-anhydride 51 was achieved by using quinine or quinidine with very high enantiomeric excess value (up to 98% ee) and with high chemical yield. The quinine-mediated desymmetrizati...
Viscoelastic properties of reactive and non-reactive styrene-maleic anhydride olefinic blends Bayram, G; Yılmazer, Ülkü; Xanthos, M (2000-05-11) Reactive blends of styrene-maleic anhydride (SMAH) with polyethylene/methyl acrylate/glycidyl methacrylate (PE-F) and non-reactive blends of SMAH with polyethylene/methyl acrylate (PE-NF) were produced and characterized in terms of morphology and viscoelastic properties in order to understand the reaction characteristics between anhydride/epoxy functional groups. Storage modulus, G', loss modulus, G " and complex viscosity, eta* of reactive blends at 25 % and 50 % PE-F were higher than those of non-reactive...
Asymmetric synthesis of norbornene based 1,4-Aminoalcohol derivatives and applications in asymmetric diethylzinc reactions Erdem, Mine; Tanyeli, Cihangir; Department of Chemistry (2007) The asymmetric synthesis of chiral norbornene based 1,4-aminoalcohols and their applications in asymmetric diethylzinc addition reactions was perfomed starting from meso-anhydride 50. The desymmetrization of this meso-anhydride 50 was done by the usage of quinine or quinidine cinchona alkaloids with very high enantiomeric excess values (up to 98% ee) and chemical yields. The Quinidine-mediated desymmetrization of meso-anhydride 50 with methanol gave (2R,3S)-(+)-cis-monoester 51. The amination of this result...
Asymmetric organocatalytic direct Mannich reaction of acetylacetone and isatin derived ketimines: Low catalyst loading in chiral cinchona-squaramides İŞİBOL, Duygu; Karahan, SEDA; Tanyeli, Cihangir (2018-02-07) A highly enantioselective synthesis of 3-amino-2-oxindoles by direct Mannich reaction between acetylacetone and N-carbamoyl isatin ketimine has been described herein. Corresponding chiral adducts were obtained in high yields (up to 98%) and with excellent enantioselectivities (up to >99% ee) by very low (1 mol%) catalyst loading of 2-adamantyl substituted bifunctional cinchona-squaramide.

Citation Formats

Ö. Doğan, 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, pp. 2099–2104, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40335.