Catalytic efficiency of primary β-amino alcohols and primary α-amino amides in enantioselective reactions of isatins

Over recent decades, enantioselective organocatalysis has garnered significant attention within the dominion of organic chemistry. This field offers the potential for intricate organic transformations with high stereoselectivity, employing small-molecule organic compounds as catalysts. Chiral primary beta-amino alcohols and primary alpha-amino amides, which feature adjacent enamine (Br & oslash;nsted base site) and hydrogen-bonding sites (Br & oslash;nsted acid site), along with flexible bulky substituents to modulate steric factors, are highly valuable multifunctional organocatalysts. Their characteristics make them cost-effective alternatives, as they are easily synthesized, airstable, and adaptable for introducing various functional groups and adjusting steric environments. Isatin derivatives, particularly 3-substituted-3-hydroxyindolin-2-ones, have garnered significant interest from both organic and medicinal chemists due to their presence in several natural products and drug candidates. Acknowledging the significance of straightforward organocatalysts and 3-substituted-3-hydroxyindolin-2-ones, this study reveals the catalytic efficiency of primary beta-amino alcohols and primary alpha-amino amides in enantioselective reactions involving isatins to produce 3-substituted-3-hydroxyindolin-2-ones.