Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction
Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, vol.14, no.2, pp.436-441, 2019 (TRDizin)
- Publication Type: Article / Article
- Volume: 14 Issue: 2
- Publication Date: 2019
- Doi Number: 10.29233/sdufeffd.649920
- Journal Name: Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi
- Journal Indexes: TR DİZİN (ULAKBİM)
- Page Numbers: pp.436-441
- Süleyman Demirel University Affiliated: Yes
Abstract
In this study, two chiral 2-(2-hydroxyaryl) alcohols (HAROLs; 1,4-diols) and a 1,4-
aminoalkylphenol (AAP) were examined as hydrogen-bond donor (HBD) organocatalysts in the
asymmetric hetero Diels-Alder (HDA) reaction of aldehydes with Rawal’s diene. Catalytic
amount (10 mol%) of the both scaffolds (HAROL and AAP) have been found to effect the HDA
reaction in a quite efficient manner. Among them, a HAROL molecule based on indan backbone
was turned out to be the best in terms of catalytic activity and enantioselectivity. On the other
hand, AAP tested seemed to act as a bifunctional organocatalyst, i.e. as both a Lewis base and
HBD organocatalyst. Experimental results underpins that a careful tuning of HAROL structure
might lead to the development of more general HBD organocatalysts.