290366-79-9Relevant academic research and scientific papers
Squaramide-Catalyzed Michael Addition as a Key Step for the Direct Synthesis of GABAergic Drugs
Veverková, Eva,Bilka, Stanislav,Baran, Rastislav,?ebesta, Radovan
, p. 1474 - 1482 (2016/05/24)
Enantioselective organocatalytic Michael additions serve as the key step in syntheses of chiral drugs based on γ-aminobutyric acid. The applicability of various squaramide catalysts for these Michael-type reactions has been assessed. Very good results in
Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: Synthesis of (R)-rolipram and (R)-baclofen
Yang, Xiao-Fei,Ding, Chang-Hua,Li, Xiao-Hui,Huang, Jian-Qiang,Hou, Xue-Long,Dai, Li-Xin,Wang, Pin-Jie
, p. 8980 - 8985,6 (2012/12/12)
The Pd-catalyzed asymmetric allylic alkylation (AAA) reaction of nitromethane with monosubstituted allyl substrates was realized for the first time to provide corresponding products in high yields with excellent regio- and enantioselectivities. The protocol was applied to the enantioselective synthesis of (R)-baclofen and (R)-rolipram.
Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: Synthesis of (R)-rolipram and (R)-baclofen
Yang, Xiao-Fei,Ding, Chang-Hua,Li, Xiao-Hui,Huang, Jian-Qiang,Hou, Xue-Long,Dai, Li-Xin,Wang, Pin-Jie
, p. 8980 - 8985 (2013/01/15)
The Pd-catalyzed asymmetric allylic alkylation (AAA) reaction of nitromethane with monosubstituted allyl substrates was realized for the first time to provide corresponding products in high yields with excellent regio- and enantioselectivities. The protocol was applied to the enantioselective synthesis of (R)-baclofen and (R)-rolipram.
Intermediate as catalyst: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides
Ogawa, Takanori,Mouri, Shinsuke,Yazaki, Ryo,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information; experimental part, p. 110 - 113 (2012/02/14)
Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides is promoted by a mesitylcopper/(R)-DTBM- Segphos precatalyst, affording γ-nitrothioamides in moderate to high syn-selectivity and excellent enantioselectivity. The inter
Catalytic asymmetric conjugate addition of nitroalkanes to 4-nitro5-styrylisoxazoles
Baschieri, Andrea,Bernardi, Luca,Ricci, Alfredo,Suresh, Surisetti,Adamo, Mauro F. A.
supporting information; experimental part, p. 9342 - 9345 (2010/03/24)
(Chemical equation presented) Nitro versus nitro: 4-Nitro-5- styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol% of a readily prepared phasetransfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).
An efficient enantioselective method for asymmetric Michael addition of nitroalkanes to α,β-unsaturated aldehydes
Wang, Yongcan,Li, Pengfei,Liang, Xinmiao,Zhang, Tony Y.,Ye, Jinxing
, p. 1232 - 1234 (2008/12/20)
The addition of nitroalkanes to α,β-unsaturated aldehydes under the catalysis of (S)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine and lithium acetate as additive afforded γ-nitroaldehydes in good yield and up to 97% ee. The Royal Society of Chemistry.
Highly enantioselective organocatalytic conjugate addition of nitromethane to α,β-unsaturated aldehydes: Three-step synthesis of optically active baclofen
Zu, Liansuo,Xie, Hexin,Li, Hao,Wang, Jian,Wang, Wei
, p. 2660 - 2664 (2008/09/19)
An efficient, organocatalytic, highly enantioselective, conjugate addition reaction of nitromethane with α,β-unsaturated aldehydes has been developed. The process serves as the key step for a practical 3-step synthesis of chiral baclofen, an antispastic drug.
Catalytic enantioselective conjugate addition of nitromethane to α′-hydroxy enones as surrogates of α,β-unsaturated carboxylic acids and aldehydes
Palomo, Claudio,Pazos, Raquel,Oiarbide, Mikel,Garcia, Jesus M.
, p. 1161 - 1164 (2007/10/03)
No base is required for the Mg(II)-catalyzed conjugate addition of nitromethane to α′-hydroxy enones in the presence of molecular sieves. Good enantioselectivities are attained using 3 or 4 A MS and about 10 mol% of Mg(OTf)2-chiral bisoxazoline
A short and convenient chemoenzymatic synthesis of both enantiomers of 3-phenylGABA and 3-(4-chlorophenyl)GABA(Baclofen)
Felluga, Fulvia,Gombac, Valentina,Pitacco, Giuliana,Valentin, Ennio
, p. 1341 - 1345 (2007/10/03)
Both enantiomers of the pharmacologically active GABA analogues 4-amino-3-phenyl and 4-amino-3-(4-chlorophenyl)butyric acid (Baclofen) with high enantiomeric excesses were synthesized by a chemoenzymatic method involving α-chymotrypsin mediated kinetic resolutions of the corresponding 3-phenyl- and 3-(4-chlorophenyl)-4-nitrobutyric acid methyl ester precursors.
Synthesis of both enantiomers of baclofen using (R)- and (S)-N-phenylpantolactam as chiral auxiliaries
Camps, Pelayo,Munoz-Torrero, Diego,Sanchez, Laura
, p. 2039 - 2044 (2007/10/03)
Esterification of racemic 4-nitro-3-(4-chlorophenyl)butanoic acid with (R)- or (S)-N-phenylpantolactam as the chiral auxiliary allowed us to obtain the (3R,3′R)- or (3S,3′S)-nitro esters with >98:2 dr after column chromatography. Hydrolysis of the resulti
