1214939-17-9Relevant academic research and scientific papers
Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds
Moriyama, Katsuhiko,Oka, Yukari,Tsuzuki, Seiji
supporting information, p. 11457 - 11460 (2021/11/12)
A chiral anthranilic pyrrolidine catalyst as a custom-made amine-catalyst was developed for the enantio- and diastereo selective Michael reaction of nitroalkenes with carbonyl compounds. In particular, a peptide-like catalyst in which an α-amino acid is a
Novel bifunctional L-prolinamide derivatives as highly efficient organocatalysts for asymmetric nitro-Michael reactions
Xu, Dan,Wang, Junliang,Yan, Lijun,Yuan, Mingquan,Xie, Xiaotian,Wang, Yongchao
, p. 1121 - 1132 (2016/11/11)
A series of novel bifunctional L-prolinamide derivatives was synthesised, of which (S)-N-((S)-2-oxo-1-phenyl-2-(tritylamino)ethyl)pyrrolidine-2-carboxamide 6 was found to be the most effective catalyst in terms of both the yield and stereoselectivity for the nitro-Michael reaction of aldehydes to nitroalkenes. Under these optimized reaction conditions, 17 corresponding novel nitro-Michael addition adducts had high yields (up to 94%) and showed excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (up to 98 ee) under mild reaction conditions.
NOVEL TRICYCLIC CHIRAL COMPOUNDS AND THEIR USE IN ASYMMETRIC CATALYSIS
-
Page/Page column 18; 25; Sheet 15, (2011/11/12)
The present invention relates to a compound of general Formula (XX), its formation and its use in asymmetric catalysis. In Formula (XX) R and R31 are independently —COOR3, —R4COOR3, —R4CHO, —R4COR3, —R4CONR5R6, —R4COX, —R4OP(═O)(OH)2, —R4P(═O)(OH)2), —R4C(O)C(R3)CR5R6 and —R4CO2COR3. In addition, R31 may also be hydrogen. R3, R5 and R6 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. R4 an aliphatic bridge with a main chain having 1 to about 20 carbon atoms, an alicyclic bridge, an aromatic bridge, an arylaliphatic bridge or an arylalicyclic bridge, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si, and X is halogen. In Formula (XX) R30 is —C(OH)R1R2 or —COOR14, wherein R1, R2 and R14 are independently hydrogen, an aliphatic group with a main chain having 1 to about 20 carbon atoms, an alicyclic group, an aromatic group, an arylaliphatic group or an arylalicyclic group, comprising 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si.
Chemzymes: A new class of structurally rigid tricyclic amphibian organocatalyst inspired by natural product
Xiao, Jian,Xu, Feng-Xia,Lu, Yun-Peng,Loh, Teck-Peng
supporting information; experimental part, p. 1220 - 1223 (2010/06/13)
"Chemical Equation Presented" A new class of structurally rigid tricyclic amphibian chiral catalyst was rationally designed based on the hexahydropyrrolo[2,3-b]indole skeleton as a new type of chemzyme. This new type of chemzyme possesses a structurally rigid tricyclic skeleton and a chiral pocket which provides a well-organized chiral environment for asymmetric induction, as well as a hydrophobic pocket to enable organocatalytic reactions to proceed smoothly both in organic solvents and in water.
