New mechanistic approach in the enamine-based asymmetric organocatalysis

During the course of my research in asymmetric organocatalysis, inversion enantioselectivity was observed aldol reactions acetone with different aldehydes catalyzed by amphiphilic proline derivatives aqueous media varying only achiral components. It not possible to explain explored dual stereocontrol existing models, therefore I proposed a new mechanism for l-amino acid and explained phenomenon structures micelle-stabilized transition state described as metal-free version Zimmerman-Traxler model explicit participation water molecule. Contrary according mechanism, formation bonds proceeds directly stabilized molecule, without additional step product iminium ion hydrolysis. The has universal character, it is consistent experimental results general theoretical conceptions, applicable all enamine-based organocatalytic carried out aqueous, but organic well, because initial catalytic cycle, which involves an enamine from carbonyl compound (derivative), liberates one