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, cilt.54, sa.42, ss.5677-5681, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 54 Sayı: 42
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.tetlet.2013.08.004
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5677-5681
  • Anahtar Kelimeler: 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
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

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.