930769-55-4Relevant academic research and scientific papers
SmI2-promoted imino-Reformatsky reaction for facile synthesis of enantioenriched β-amino acid esters
Wang, Li,Shen, Chun,Xu, Ming-Hua
experimental part, p. 61 - 65 (2011/12/15)
A facile and efficient method for the stereoselective synthesis of β-amino acid esters via SmI2-promoted imino-Reformatsky reaction is described. Asymmetric addition of tert-butyl bromoacetate to N-tert-butanesulfinyl aldimines afforded β-amino
A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams
Forro, Eniko,Paal, Tihamer,Tasnadi, Gabor,Fueloep, Ferenc
, p. 917 - 923 (2007/10/03)
A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).
A one-pot synthesis of 3-amino-3-arylpropionic acids
Tan,Weaver
, p. 7449 - 7461 (2007/10/03)
3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these β-amino acids. The reaction mechanism of this one-pot synthesis of β-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed.
