Premium
Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules
Author(s) -
RuízPérez Karen M.,
QuirozGarcía Beatriz,
HernándezRodríguez Marcos
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800886
Subject(s) - chemistry , catalysis , supramolecular chemistry , amide , combinatorial chemistry , selectivity , adduct , hydrogen bond , solubility , organocatalysis , organic chemistry , enantioselective synthesis , molecule
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 is the self‐assembly capability with complementary modules by Watson–Crick interactions. These supramolecular adducts behave differently from the catalyst alone, some of them have lower performance but others improve the selectivity of the product. Therefore, this approach avoids the synthesis of many catalysts.