Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes

Karakaya I., KARABUĞA Ş., ALTUNDAŞ R., ULUKANLI S.

TETRAHEDRON, cilt.70, sa.44, ss.8385-8388, 2014 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 44
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tet.2014.08.067
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8385-8388
  • Atatürk Üniversitesi Adresli: Evet

Özet

Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the optimised reaction conditions, the best enantioselectivity was obtained using L-lactic acid derived 4-phenylquinazolinol and apart from the cyclohexylcarbaldehyde derivative, 16 propargylic alcohols were then synthesised in moderate to excellent enantiomeric excess from 53% to 97%. (C) 2014 Elsevier Ltd. All rights reserved.