Abstract
New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.
Highlights
The aldol reaction is an important tool in organic chemistry to synthesize attractive intermediates
In our continuing research on the synthesis of chiral organocatalysts and their investigation in direct asymmetric aldol reaction, we have investigated the catalytic potential of some proline amide derivatives and 1,2,3,4-tetrahydroisoquinoline and thiazolidine-4-carboxylic acid amide derivatives.[33,34,35,36]
Among the catalysts investigated in this study, catalyst 7c gave the best diastereoselectivities, enantioselectivities and yields when different aliphatic ketones and aromatic aldehydes with electron withdrawing groups were used
Summary
The aldol reaction is an important tool in organic chemistry to synthesize attractive intermediates. This carbon-carbon bond formation reaction yields the β-hydroxyketones which are important precursors for pharmaceuticals and natural products. The asymmetric version of the reaction has been extensively studied and used for the synthesis of valuable intermediates, highly functionalized and complex molecules with important biological activities. The most considerable asymmetric method is the using of asymmetric organocatalysis which. Keskin et al.: Synthesis of New Di- and Triamides. 2020, 67, 1014–1023 are non-metal, small, synthesizable organic compounds with low toxicity and mostly natural products. Slov. 2020, 67, 1014–1023 are non-metal, small, synthesizable organic compounds with low toxicity and mostly natural products.
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