35388-38-6Relevant articles and documents
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
Gagnot, Glwadys,Hervin, Vincent,Coutant, Eloi P.,Desmons, Sarah,Baatallah, Racha,Monnot, Victor,Janin, Yves L.
supporting information, p. 2846 - 2852 (2018/11/27)
We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes
Efimova,Ozerova,Novikova,Baichurin,Berestovitskaya
, p. 1496 - 1499 (2015/01/09)
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)-ethenes proceed via initial formation the aza-Michael product, are accompanied by liberation of nitroacetic ester (or nitroacetophenone), and result in N-aryl(het
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes
Efimova,Ozerova,Novikova,Baichurin,Berestovitskaya
, p. 1496 - 1499 (2015/02/19)
Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)-ethenes proceed via initial formation the aza-Michael product, are accompanied by liberation of nitroacetic ester (or nitroacetophenone), and result in N-aryl(het
Nucleophilic addition to nitroacrylates: application towards the synthesis of 2,3-dehydroamino acids and 2,3-diamino acids
Lewandowska, Elzbieta,Wichlacz, Kinga,Sobczak, Adam J.
body text, p. 152 - 156 (2010/03/01)
The addition of the N-pronucleophiles to 2- or 3-nitro-2-alkenoates in the presence of base provided Michael addition products. In the case of 3-nitro compounds, reaction occurred via the formation of α-adducts and the subsequent elimination of nitrous ac
A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride
Hirotani, Seiko,Kaji, Eisuke
, p. 4255 - 4270 (2007/10/03)
Titanium tetrachloride-induced cyclization of 3-(o- or m-substituted p- methoxyphenyl)-2-nitro acrylates (1) provided stereoselectively (4α,5β)-1- oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p- methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-1'- naphthyl)-2-nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4α,5β)-4'-oxospiro[isoxazole(4H)5,1'(4'H)-naphthatene]. 3- (10'-methoxy-9'-anthryl)-2-nitroacrylate was converted to 10- oxospiro[anthracene-(10H)9,5'(4'H)-isoxazole].
Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes
Versleijen, Jos P. G.,Van Leusen, Albert M.,Feringa, Ben L.
, p. 5803 - 5806 (2007/10/03)
The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) w
