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Proline-calixarene thiourea host-guest complex catalyzed enantioselective aldol reactions: from nonpolar solvents to the presence of water

2014-03-15
Demircan, Ezgi
EYMUR, SERKAN
Demir, Ayhan Sıtkı
A proline-calix[4]arene thiourea host-guest complex catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone has been developed. The anti-configured products were obtained in good yields and with high enantioselectivities. The reaction is proposed to work via a modified Houk-List model, where the carboxylate part of the praline constitutes as a supramolecular system with the thiourea. The outcome of the study indicates the influence of the calix[4]arene thiourea on both the reactivity and selectivity in a non-polar reaction medium, even in the presence of water at moderate temperatures.