Imidazolidinone intermediates in prolinamide-catalyzed aldol reactions.

Interfacial catalysis of aldol reactions by prolinamide surfactants in reverse micelles.

L-Proline and their derivatives are among the most important class of organic catalysts. Three prolinamide surfactants were designed and synthesized. Although the surfactants carried identical catalytic groups, their headgroups contained different functionalities that affected their ability to self-assemble under reverse micelle conditions and hydrogen-bond with the reactants. The surfactant wi...

Novel carbohydrate-derived prolinamide as a highly efficient, recoverable catalyst for direct aldol reactions in water

Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions.

(S(a))-Binam-D-prolinamide (20 mol%), instead of (S(a))-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to ...

Enantioselective direct aldol reactions catalyzed by L-prolinamide derivatives.

l-Prolinamides 2, prepared from l-proline and simple aliphatic and aromatic amines, have been found to be active catalysts for the direct aldol reaction of 4-nitrobenzaldehyde with neat acetone at room temperature. They give moderate enantioselectivities of up to 46% enantiomeric excess (ee). The enantioselectivity increases as the amide N-H becomes a better hydrogen bond donor. l-Prolinamides ...

Prolinethioamides versus Prolinamides in Organocatalyzed Aldol Reactions - A Comparative Study

Various organocatalysts have been developed for the aldol reaction but particular attention has been paid to prolinamide derivatives. They are easy to prepare and their catalytic activity can be readily tuned through structural modification. In this review, the comparison of catalytic activities between prolinethioamides and their respective amides in direct asymmetric aldol reactions is presen...