Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts

DİLEK Ö., Tezeren M. A., TİLKİ T., Ertürk E.

Tetrahedron, cilt.74, sa.2, ss.268-286, 2018 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 74 Sayı: 2
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.tet.2017.11.054
  • Dergi Adı: Tetrahedron
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.268-286
  • Anahtar Kelimeler: Chiral 1,4-diols, Chiral ligands, Diethylzinc addition, Hydrogen-bond donor organocatalysts, Morita-Baylis-Hillman reaction
  • Isparta Uygulamalı Bilimler Üniversitesi Adresli: Evet

Özet

Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the 1,2-addition of certain organometallic compounds to aldehydes in the presence of Ti(OiPr)4 (up to 97% y, 88% ee) and performed as a hydrogen-bond donor organocatalyst in the Morita-Baylis-Hillman reaction, promoted by trialkylphosphines.