Catalytic asymmetric one-pot synthesis of pyrrolidines via 1,3-dipolar cycloaddition reaction of azomethine ylides


Tezin Türü: Yüksek Lisans

Tezin Yürütüldüğü Kurum: Orta Doğu Teknik Üniversitesi, Fen Edebiyat Fakültesi, Kimya Bölümü, Türkiye

Tezin Onay Tarihi: 2013

Öğrenci: SEYLAN AYAN

Danışman: ÖZDEMİR DOĞAN

Özet:

In recent years one-pot reactions have been studied significiantly by different research groups. These reactions provide complex molecules from very simple starting materials in a single step. For that reason it is considered as atom economical reaction and “green chemistry”. Asymmetric versions of these reactions are also being studied by organic groups for the synthesis of complex chiral compounds. In this respect, we have studied metal catalyzed one-pot reaction of azomethine ylides with electron defficient dipolarophiles using chiral ligands with silver metal. As the chiral ligands amino alcohol based ferrocenyl aziridinyl methanol (FAM) and phosphorous based phosphino ferrocenyl aziridinyl methanol (PFAM) were used. These ligands have an advantage of being synthesized easily on a gram scale starting from acryloyl ferrocene. Moreover, the yellow color of ferrocene ease the purification by flash column chromatography. For the one-pot reaction glycine methyl ester, aromatic aldehyde, dipolarophile, chiral ligand, and silver salt were mixed in the same reaction flask to form pyrrolidine derivatives. Analysis of the reaction products showed that pyrrolidine derivatives can be obtained with up to 99% yield and 86% enantioselectivity by this catalytic asymmetric one-pot reaction.