1052183-73-9Relevant academic research and scientific papers
Highly Enantioselective Michael Addition of Nitroalkanes to Enones and Its Application in Syntheses of (R)-Baclofen and (R)-Phenibut
Guo, Xing-Tao,Shen, Jie,Sha, Feng,Wu, Xin-Yan
, p. 2063 - 2072 (2015)
A highly enantioselective Michael addition of nitroalkanes to α,β-unsaturated ketones was developed. In the presence of a chiral primary amine-thiourea catalyst based on dehydroabietic amine, γ-nitro ketones were obtained with excellent enantioselectiviti
Optically Active 4-Substituted 5-Nitropentan-2-ones: Valuable Chiral Building Blocks for the Stereocontrolled Construction of Spiro-Pyrazolone Scaffolds with Five Contiguous Stereogenic Centers
Sun, Jiao,Jiang, Cuiping,Zhou, Zhenghong
, p. 1165 - 1172 (2016)
The application of readily available optically active 4-substituted 5-nitropentan-2-ones as chiral building blocks in the stereocontrolled construction of spiro-pyrazolone scaffolds was investigated. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (
Asymmetric Conjugate Addition of Nitroalkanes to Enones Using a Sulfonamide-Thiourea Organocatalyst
Kawada, Masahiro,Nakashima, Kosuke,Hirashima, Shin-Ichi,Yoshida, Akihiro,Koseki, Yuji,Miura, Tsuyoshi
, p. 6986 - 6991 (2017)
The asymmetric conjugate addition of nitroalkanes to α,β-unsaturated ketones in the presence of a catalytic amount of a novel sulfonamide-thiourea organocatalyst resulted in the corresponding γ-nitro carbonyl products in high yields with excellent enantio
Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights
Ueda, Atsushi,Umeno, Tomohiro,Doi, Mitsunobu,Akagawa, Kengo,Kudo, Kazuaki,Tanaka, Masakazu
, p. 6343 - 6356 (2016/08/16)
Helical peptide foldamer catalyzed Michael addition reactions of nitroalkane or dialkyl malonate to α,β-unsaturated ketones are reported along with the mechanistic considerations of the enantio-induction. A wide variety of α,β-unsaturated ketones, including β-aryl, β-alkyl enones, and cyclic enones, were found to be catalyzed by the helical peptide to give Michael adducts with high enantioselectivities (up to 99%). On the basis of X-ray crystallographic analysis and depsipeptide study, the amide protons, N(2)-H and N(3)-H, at the N terminus in the α-helical peptide catalyst were crucial for activating Michael donors, while the N-terminal primary amine activated Michael acceptors through the formation of iminium ion intermediates.
C3-symmetric proline-functionalized organocatalysts: Enantioselective michael addition reactions
Moorthy, Jarugu Narasimha,Saha, Satyajit
experimental part, p. 6359 - 6365 (2011/03/17)
C3-Symmetric, tripodal catalyst 4 based on 1,3,5- triethylbenzene, which incorporates the features of a molecular receptor, is shown to catalyze Michael addition reactions ofcarbonyl compounds to β-nitrostyrenes in a high stereoselectivity (up to 99:1a dr and up to 98%ee). Copyright
Primary amine-thioureas based on tert-butyl esters of natural amino acids as organocatalysts for the Michael reaction
Kokotos, Christoforos G.,Kokotos, George
experimental part, p. 1355 - 1362 (2009/12/09)
A new class of primary amine-thioureas based on tert-butyl esters of (S)-α-amino acids and (1S,2S)-diphenylethylenediamine was synthesized and their activity as catalysts in Michael additions was evaluated. Derivatives based on di-tert-butyl aspartate and
A novel bifunctional sulfonamide primary amine-catalyzed enantioselective conjugate addition of ketones to nitroolefins
Xue, Fei,Zhang, Shilei,Duan, Wenhu,Wang, Wei
supporting information; experimental part, p. 2194 - 2198 (2009/10/02)
The enantioselective conjugate addition of a variety of ketones to nitroolefins has been developed. The process is efficiently catalyzed by a novel bifunctional sulfonamide primary amine in good yields and with good levels of enantioselectivity.
Asymmetric multifunctional organocatalytic Michael addition of nitroalkanes to α,β-unsaturated ketones
Li, Pengfei,Wang, Yongcan,Liang, Xinmiao,Ye, Jinxing
supporting information; experimental part, p. 3302 - 3304 (2009/02/04)
Cinchona alkaloid derived primary amine thioureas organocatalyzed Michael addition of nitroalkanes to enones in good yield and up to 98% ee and offered a new way to construct quaternary stereocenters from enones and nitroalkanes. The Royal Society of Chem
