Novel supramolecular organocatalyst for asymmetric aldol reactions


Thesis Type: Postgraduate

Institution Of The Thesis: Middle East Technical University, Turkey

Approval Date: 2013

Thesis Language: English

Student: Ezgi Demircan

Co-Supervisor: CİHANGİR TANYELİ, AYHAN SITKI DEMİR

Abstract:

The proline–calix[4]arene thiourea host–guest complex catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone is developed. The anti-configured products were obtained in good yields and high enantioselectivities. The reaction is proposed to work via modified Houk–List model, where the carboxylate part of the proline constitutes a supramolecular system with the thiourea. The outcome of the study indicates the influence of the calix[4]arene thiourea on the reactivity and selectivity in a non-polar reaction medium, even in the presence of water at moderate temperatures.