Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
Tetrahedron, vol.74, no.2, pp.268-286, 2018 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 74 Issue: 2
- Publication Date: 2018
- Doi Number: 10.1016/j.tet.2017.11.054
- Journal Name: Tetrahedron
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.268-286
- Keywords: Chiral 1,4-diols, Chiral ligands, Diethylzinc addition, Hydrogen-bond donor organocatalysts, Morita-Baylis-Hillman reaction
- Isparta University of Applied Sciences Affiliated: Yes
Abstract
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.