1076243-71-4Relevant academic research and scientific papers
Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds
Quintard, Adrien,Belot, Sebastien,Marchai, Estelle,Alexakis, Alexandre
supporting information; experimental part, p. 927 - 936 (2010/04/25)
The substitution of the 4-position of hydroxyproline by a phenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the α-functionalization of a wide range of linear/ branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and α-amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.
Diversity-oriented synthesis towards conceptually new highly modular aminal-pyrrolidine organocatalysts
Quintard, Adrien,Bournaud, Chloee,Alexakis, Alexandre
supporting information; experimental part, p. 7504 - 7507 (2009/08/14)
A study was conducted to demonstrate the synthesis of animal-pyrrolidine derivatives and their applications in various Michael addition reactions. The animal-pyrrolidine organocatalysts were prepared from protected L-prolinal, which was obtained from commercially available Cbz-L-proline. Animal formations with various reoisomers were prepared, while catalysts were synthesized, to study the influence of the different substituents. It was observed that all catalysts were stable after prolonged conservation period. The newly synthesized catalysts were also tested in the reaction of proopinaldehyde with nitrostyrene. It was also observed that all the catalysts lead to full conversion after a short reaction time. The enantioselectivity varied from 49% in diastereoisomeric catalyst, to the best enantioselectivity of 79%, using reoisomer catalysts.
