247134-05-0Relevant academic research and scientific papers
Regioselectivity of the Conjugate Addition of Amines to Dissymmetrical Pull-Pull Alkenes
Maddaluno, Jacques,Rulev, Alexander Yu.,Semenov, Valentin A.,Ushakov, Igor A.,Vashchenko, Alexander V.,Zubkov, Ilya N.
, p. 3278 - 3288 (2021)
The regioselectivity of the conjugate nucleophilic addition of amines to vicinal di-acceptor-substituted alkenes has been studied. A set of results obtained with standard primary and secondary amines gives some clues on the relative acceptor character of classical electron-withdrawing groups (EWG). We have shown in addition that computed inverse local nucleophilicity index can be used to predict the regioselectivity of the nucleophilic attack.
Practical, highly enantioselective chemoenzymatic one-pot synthesis of short-chain aliphatic β-amino acid esters
Wei?, Markus,Gr?ger, Harald
experimental part, p. 1251 - 1254 (2009/09/06)
A practical, highly enantioselective method for the synthesis of short-chain aliphatic β-amino acid esters was developed starting from prochiral and easily accessible substrates. This chemoenzymatic approach is based on a nonenzymatic aza-Michael addition
Barbier conditions for reformatsky and alkylation reactions on trifluoromethyl aldimines
Dos Santos, Mickael,Crousse, Benoit,Bonnet-Delpon, Danièle
, p. 399 - 401 (2008/09/16)
β-Trifluoromethyl β-amino acids and α-trifluoromethyl α-alkyl amines can be easily prepared under Barbier conditions from trifluoromethyl aldimines in moderate to good yields. β-Trifluoromethyl β-amino acids were obtained in good enantioselectivity from t
Stereoselective synthesis of fluorinated β-aminoacids from ethyl trans- N-benzyl-3-trifluoromethylaziridine-2-carboxylate
Davoli, Paolo,Forni, Arrigo,Franciosi, Chiara,Moretti, Irene,Prati, Fabio
, p. 2361 - 2371 (2007/10/03)
trans-N-Benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtainable in enantiopure forms by CAL-catalysed enzymatic resolution, allowed the regio- and stereoselective synthesis of chiral fluorinated anti- α-functionalised-β-aminoacids, such as trifluoroisoserinates or trifluoro- β-alanine, and trans-3-halo- or 3-hydroxy-β-lactams. Starting from the enantiomerically pure methyl analogue of the title compound, 2c, pure enantiomers of trifluoroisoserine can be obtained in high overall chemical yield. Absolute configurations of optically active β-aminoacids were determined by chemical correlation.
