Synthesis of a bipyridine-derived achiral thiourea trifluoromethanesulfonic acid salt and its application as an additive in organocatalytic asymmetric reactions

Demir A. S., BAŞÇEKEN S.

TETRAHEDRON LETTERS, vol.54, no.42, pp.5677-5681, 2013 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 42
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetlet.2013.08.004
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5677-5681
  • Keywords: Host-guest complex, Proline-thiourea interaction, Asymmetric aldol reaction, Enantioselective Michael reaction, Asymmetric Mannich reaction, DIRECT ALDOL REACTION, SMALL ORGANIC-MOLECULES, HIGHLY EFFICIENT, MICHAEL-ADDITION, N-PROLYLSULFONAMIDE, ALDEHYDES, CATALYSTS, MANNICH, CYCLOHEXANONE, PROLINES
  • Middle East Technical University Affiliated: No

Abstract

The host-guest complex of a proline-thiourea bipyridine trifluoromethanesulfonic acid salt can catalyze organocatalytic asymmetric reactions such as aldol, Michael, and Mannich in polar protic medium with high stereoselectivities. The privileged bipyridine backbone and the thiourea motif are essential to the activity and enantioselectivity through hydrogen bonding interactions. (C) 2013 Elsevier Ltd. All rights reserved.