1254178-79-4Relevant academic research and scientific papers
Functionalized proline with double hydrogen bonding potential: Highly enantioselective Michael addition of carbonyl compounds to β-nitrostyrenes in brine
Saha, Satyajit,Seth, Saona,Moorthy, Jarugu Narasimha
supporting information; experimental part, p. 5281 - 5286 (2010/11/03)
Simple synthetic manipulation of S-proline allows access to prolinamides 5-7 as organocatalysts capable of double hydrogen bonding for enantioselective Michael addition reactions of carbonyl compounds to β-nitrostyrenes. It is shown that prolinamide catalyst 7 leads to addition products with a high diastereo- as well as enantioselectivity. The transition state structure involving the binding of electrophilic nitrostyrene via two H-bonds is believed to be further stabilized by π,π stacking interactions mediated by the tosyl ring.
