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

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–...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2014-03, Vol.25 (5), p.443-448
Main Authors: Demircan, Ezgi, Eymur, Serkan, Demir, Ayhan Sıtkı
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 proline 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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2014.01.015