Abstract
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 presented.
Highlights
Organocatalysis can be defined as the acceleration of a chemical reaction using a substoichiometric amount of an organic compound
The concept was confirmed by Tang and Jiang who discovered that simple L-prolinamides were able to catalyze the reaction of benzaldehydes with acetone giving aldols in good yields but with low enantioselectivities [18]
When aminoalcohols were used in the synthesis of amide 3 in place of the amine, the hydroxy group was preferentially protected with TBDMS since this allowed both the
Summary
Organocatalysis can be defined as the acceleration of a chemical reaction using a substoichiometric amount of an organic compound. Until 2000, only a limited number of preparatively useful applications had been reported, with one of the most important being the proline catalyzed synthesis of Wieland-Miescher ketone [9,10]. In 2004, three groups independently reported a proline derived tetrazol catalyst and showed that the carboxyl group could be replaced with a group possessing a proton of reasonable acidity [15,16,17]. The concept was confirmed by Tang and Jiang who discovered that simple L-prolinamides were able to catalyze the reaction of benzaldehydes with acetone giving aldols in good yields but with low enantioselectivities [18]. Particular focus will be placed on the relationship between L-prolinamide and L-prolinethioamide structure, acidity and their catalytic activity in the aldol reaction
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