74282-81-8Relevant academic research and scientific papers
Enantioselective conjugate addition of ketones to nitroalkenes catalyzed by pyrrolidine-sulfamides
Wang, Jinjia,Lao, Jinhua,Du, Quansheng,Nie, Shaozhen,Hu, Zhipeng,Yan, Ming
experimental part, p. 232 - 238 (2012/06/01)
A series of chiral pyrrolidine-sulfamides were prepared and examined as the catalysts for conjugate addition of ketones to nitroalkenes. Benzoic acid was identified as the most efficient additives for the transformation. Excellent enantioselectivities, diastereoselectivities, and yields were achieved for the reaction of cyclohexanone with β-aryl nitroethylenes under solvent free conditions. β-Isopropyl nitroethylene is also applicable and the product could be obtained with excellent enantioselectivity after extended reaction time. A comparison of the catalytic behaviors of pyrrolidine-sulfamide organocatalysts with different side chains demonstrates that the enantioselectivity is mainly controlled by the chiral pyrrolidine unit and the additional chiral center at the side chain exerts neglectable effects. The H-bonding interaction between the sulfamide and the nitro group is proposed to be crucial for the activation of the nitroalkene and the constitution of well-organized transition state. Copyright
Pyrrolidinyl-sulfamide derivatives as a new class of bifunctional organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
Chen, Jia-Rong,Fu, Liang,Zou, You-Quan,Chang, Ning-Jie,Rong, Jian,Xiao, Wen-Jing
supporting information; experimental part, p. 5280 - 5287 (2011/08/07)
A series of chiral pyrrolidinyl-sulfamide derivatives have been identified as efficient bifunctional organocatalysts for the direct Michael addition of cyclohexanone to a wide range of nitroalkenes. The desired Michael adducts were obtained in high chemical yields and excellent stereoselectivities (up to 99/1 dr and 95% ee). The Royal Society of Chemistry 2011.
Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides
Zhang, Xue-Jing,Liu, Sheng-Ping,Li, Xue-Ming,Yan, Ming,Chan, Albert S. C.
supporting information; experimental part, p. 833 - 835 (2009/07/10)
Chiral bifunctional sulfamides were found to be highly efficient organocatalysts for the conjugate addition of aldehydes to nitroolefins in the presence of base additives. The Royal Society of Chemistry.
Synthetic homoserine lactone-derived sulfonylureas as inhibitors of Vibrio fischeri quorum sensing regulator
Frezza, Marine,Soulere, Laurent,Reverchon, Sylvie,Guiliani, Nicolas,Jerez, Carlos,Queneau, Yves,Doutheau, Alain
, p. 3550 - 3556 (2008/12/20)
A series of 9 homoserine lactone-derived sulfonylureas substituted by an alkyl chain, some of them bearing a phenyl group at the extremity, have been prepared. All compounds were found to inhibit the action of 3-oxo-hexanoyl-l-homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri, the aliphatic compounds being more active than their phenyl-substituted counterparts. Molecular modelling studies performed on the most active compound in each series suggest that the antagonist activity could be related to the perturbation of the hydrogen-bond network in the ligand-protein complexes.
