1172607-95-2Relevant academic research and scientific papers
One-pot lipase-catalyzed enantioselective synthesis of (r)-(?)-n-benzyl-3-(benzylamino)butanamide: The effect of solvent polarity on enantioselectivity
Ortega-Rojas, Marina A.,Rivera-Ramírez, José Domingo,ávila-Ortiz, C. Gabriela,Juaristi, Eusebio,González-Mu oz, Fernando,Castillo, Edmundo,Escalante, Jaime
, (2017)
The use of the solvent engineering has been applied for controlling the resolution of lipase-catalyzed synthesis of β-aminoacids via Michael addition reactions. The strategy consisted of the thermodynamic control of products at equilibrium using the lipase CalB as a catalyst. The enzymatic chemo- and enantioselective synthesis of (R)-(?)-N-benzyl-3-(benzylamino)butanamide is reported, showing the influence of the solvent on the chemoselectivity of the aza-Michael addition and the subsequent kinetic resolution of the Michael adduct; both processes are catalyzed by CalB and both are influenced by the nature of the solvent medium. This approach allowed us to propose a novel one-pot strategy for the enzymatic synthesis of enantiomerically enriched β-aminoesters and β-aminoacids.
Towards a greener synthesis of (S)-3-aminobutanoic acid: Process development and environmental assessment
Weiss, Markus,Brinkmann, Tobias,Groeger, Harald
supporting information; experimental part, p. 1580 - 1588 (2010/12/19)
An improved, greener process for the enantioselective chemoenzymatic synthesis of (S)-3-aminobutanoic acid has been developed. Reaction steps comprise an initial aza-Michael addition starting from cheap prochiral compounds, subsequent enzymatic resolution via aminolysis using commercially available Candida antarctica lipase B in a solvent-free one-pot process, hydrolysis of the resulting ester and removal of the N-benzyl moiety via hydrogenation. After isolation, the desired (S)-3-aminobutanoic acid was obtained in an overall yield of 28% and with an excellent enantiomeric excess of 99% ee. Notably, this reaction sequence does not require column chromatography with organic solvents and only one purification step of an intermediate is needed. The environmental impact of this optimized process has been evaluated and an E-factor of 41 has been calculated for the overall process. A comparative assessment with the previous process was done via mass balancing using the E-factor, the selectivity index S-1 as well as an SHE assessment.
Practical, highly enantioselective chemoenzymatic one-pot synthesis of short-chain aliphatic β-amino acid esters
Wei?, Markus,Gr?ger, Harald
scheme or table, 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
