Asymmetric Synthesis of Pyrrolidines by 1,3-Dipolar Cycloaddition Reaction; from Chiral Auxiliaries to Metal Catalysts and Organocatalysts



Asymmetric synthesis of 2,3-dihydrofurans with bifunctional quinine / squaramide organocatalysts
Bozdemir, Merve; Tanyeli, Cihangir; Department of Chemistry (2019)
Organocatalytic asymmetric reactions are efficient and environmentally friendly methods to synthesize products with higher enantioselectivities. Asymmetric domino Michael-SN2 reactions are one of the type of organocatalytic reaction frequently used to form carbon-carbon bonds in the synthesis of the derivatives of dihydrofurans, which are intermediates mainly utilized as precessor materials in the pharmaceutical fields. In this thesis, the reaction occuring between acetylacetone and (Z)-(2-bromo-2-nitroviny...
Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
Tanyeli, Cihangir; ERDEM, Mine; ÇAKIR, Esen; KESKİN, Eda (Elsevier BV, 2007-09-27)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. ...
Asymmetric synthesis of tetrahydrothiophenes in the presence of bifunctional organocatalysts
Tümer, Mustafa Faik; Tanyeli, Cihangir; Department of Chemistry (2021-1-22)
In general, nitroolefins are convenient structures as Michael acceptors. To make it clear for this work, attack of a sulfur-containing nucleophile to a nitroolefin forms a C-S bond and opening the double bond would create a nucleophilic center on the nitroolefin which leads to the formation of a new C-C bond. In this study, asymmetric organocatalytic sulfa-Michael addition of 1,4-dithiane-2,5-diol to trans-β-nitrostyrene derivatives was carried out which yielded polyfunctional tetrahydrothiophenes that have...
Asymmetric synthesis of beta-hydroxy phoshponates via benzaldehyde lyase catalyzed cross acyloin reactions
Kazancı, Ceren; Özçubukçu, Salih; Son, Çağdaş Devrim; Department of Biotechnology (2014)
Synthetically useful asymmetric cross acyloin reactions with functionalized aliphatic aldehyde have a broad range of application. The products of acyloin reactions are α-hydroxy ketone which are the subunits in several compounds and can be found in many biologically important compounds. Phosphonates can be used as an intermediate in the synthesis of potentially significant peptide analogues, catalytic antibodies, and phosphonic acid-based antibiotics which are also acknowledged as biologically important com...
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, “Asymmetric Synthesis of Pyrrolidines by 1,3-Dipolar Cycloaddition Reaction; from Chiral Auxiliaries to Metal Catalysts and Organocatalysts,” presented at the 5th Organic Chemistry Congress, Malatya, Türkiye, 2021, Accessed: 00, 2022. [Online]. Available: