Efficient access to general α-tertiary amines via water-accelerated organocatalytic multicomponent allylation.

ABSTRACT: A tetrasubstituted carbon atom connected by three sp³ or sp²-carbons with single nitrogen, i.e., the α-tertiary amine (ATA) functional group, is an essential structure of diverse naturally occurring alkaloids and pharmaceuticals. The synthetic approach toward ATA structures is intricate, therefore, a straightforward catalytic method has remained a substantial challenge. Here we show an efficient water-accelerated organocatalytic method to directly access ATA incorporating homoallylic amine structures by exploiting readily accessible general ketones as useful starting material. The synergistic action of a hydrophobic Brønsted acid in combination with a squaramide hydrogen-bonding donor under aqueous condition enabled the facile formation of the desired moiety. The developed exceptionally mild but powerful system facilitated a broad substrate scope, and enabled efficient multi-gram scalability.

SUBMITTER: Goswami P 

PROVIDER: S-EPMC9110412 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature