2018
DOI: 10.1002/ejoc.201800886
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Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules

Abstract: We report the synthesis and evaluation of prolinamide organocatalysts that incorporate aminouracils. The features of these catalysts are enhanced NH acidity of the amide because of the electron‐withdrawing nature of the heterocycle, an additional hydrogen‐bond donor at the α or β positions of this functional group (using 6‐aminouracil or 5,6‐diaminouracil respectively), and it can be recovered due to its low solubility and used again without decreasing the enantioselectivity. A unique feature of these systems … Show more

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Cited by 5 publications
(2 citation statements)
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“…The substrate scope of the aldol reaction using catalyst 1a and cyclohexanone was then investigated with various benzaldehydes (Table 3). 12,14 Good stereoselectivities were observed for all the benzaldehydes, with ee's ranging from 93% to 99% (Table 3, entries 1-4). However, the use of aldehydes with electron-donating groups decreased the yield (Table 3, entry 4).…”
Section: Resultsmentioning
confidence: 97%
“…The substrate scope of the aldol reaction using catalyst 1a and cyclohexanone was then investigated with various benzaldehydes (Table 3). 12,14 Good stereoselectivities were observed for all the benzaldehydes, with ee's ranging from 93% to 99% (Table 3, entries 1-4). However, the use of aldehydes with electron-donating groups decreased the yield (Table 3, entry 4).…”
Section: Resultsmentioning
confidence: 97%
“…During the last years, L-proline-based compounds have been successfully employed in asymmetric organocatalysis enlarging the scope of the natural amino acid. [38][39][40][41] In this context, we decided to evaluate the catalytic properties of the proline-based compound 35.…”
mentioning
confidence: 99%