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

Demircan E., EYMUR S., Demir A. S.

TETRAHEDRON-ASYMMETRY, cilt.25, sa.5, ss.443-448, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 25 Sayı: 5
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tetasy.2014.01.015
  • Dergi Adı: TETRAHEDRON-ASYMMETRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.443-448
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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. (C) 2014 Elsevier Ltd. All rights reserved.