Chiral thiourea derivatives as organocatalyts in the enantioselective Morita- Baylis-Hillman reactions

AYDIN A. E.

Arkivoc, cilt.2020, sa.6, 2020 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2020 Sayı: 6
  • Basım Tarihi: 2020
  • Doi Numarası: 10.24820/ark.5550190.p011.072
  • Dergi Adı: Arkivoc
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Directory of Open Access Journals
  • Anahtar Kelimeler: Chiral thiourea derivatives, Intermolecular Morita-Baylis-Hillman reaction, Intramolecular Morita-Baylis-Hillman reaction reaction, β-amino alcohol
  • Hatay Mustafa Kemal Üniversitesi Adresli: Evet

Özet

Novel chiral bifunctional thiourea derivatives have been synthesised and successfully applied to the intermolecular Morita-Baylis-Hillman (MBH) reaction of an aromatic aldehyde with methyl vinyl ketone (MVK) and to the intramolecular MBH reaction of ω-formyl-enone. The corresponding products were obtained with high enantioselectivities (up to 98% ee). The thiourea organocatalyst derived from a β-amino alcohol gave high enantioselectivities (92% ee) in the intermolecular MBH reaction, whereas the same chiral ligand afforded the corresponding product in high yield (85%) with moderate enantioselectivity (75% ee) in the intramolecular MBH reaction. The use of a thiophene ring-containing thiourea derivative gave high enantioselectivities in the intermolecular and intramolecular MBH reactions (85% and 95% ee, respectively).