Description:
<p>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 theasymmetric hetero Diels-Alder (HDA) reaction of aldehydes with Rawal’s diene. Catalyticamount (10 mol%) of the both scaffolds (HAROL and AAP) have been found to effect the HDAreaction in a quite efficient manner. Among them, a HAROL molecule based on indan backbonewas turned out to be the best in terms of catalytic activity and enantioselectivity. On the otherhand, AAP tested seemed to act as a bifunctional organocatalyst, i.e. as both a Lewis base andHBD organocatalyst. Experimental results underpins that a careful tuning of HAROL structuremight lead to the development of more general HBD organocatalysts. <br></p>