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

• Published in: Tetrahedron Vol. 162; p. 134124
• Main Authors: Subba Reddy, Ummareddy Venkata, Anusha, Bheemreddy, Kumar, Marri Naveen, Kothapalli, Raveendra Babu, Seki, Chigusa, Okuyama, Yuko, Kwon, Eunsang, Tokiwa, Michio, Tokiwa, Suguru, Takeshita, Mitsuhiro, Nakano, Hiroto
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 03-08-2024
• Subjects: Asymmetric organic transformations; Bifunctional organocatalysts; Enamine bonding; Organocatalysis; Primary α-amino amides; Primary β-amino alcohols; Primary β-amino alcohols; Bifunctional organocatalysts; Primary α-amino amides; Organocatalysis; Enamine bonding; Asymmetric organic transformations
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2024.134124

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 β-amino alcohols and primary α-amino amides, which feature adjacent enamine (Brønsted base site) and hydrogen-bonding sites (Brønsted 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, air-stable, 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 β-amino alcohols and primary α-amino amides in enantioselective reactions involving isatins to produce 3-substituted-3-hydroxyindolin-2-ones.
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