Chiral 1,4-Hydroxyarylalcohols (HAROLs) and 1,4-Aminoalkylphenols (AAPs) as Organocatalysts for Asymmetric Hetero Diels-Alder Reaction

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Ertürk E., Tezeren M. A., Tilki T.

Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, vol.14, no.2, pp.436-441, 2019 (Peer-Reviewed Journal)


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.