220090-79-9Relevant academic research and scientific papers
A new diastereoselective synthesis of anti-α-alkyl α-hydroxy β-amino acids
Cardillo, Giuliana,Tolomelli, Alessandra,Tomasini, Claudia
, p. 155 - 161 (2007/10/03)
As part of an ongoing project concerning the synthesis of enantiomerically pure α-hydroxy β-amino acids, we have now developed a general strategy allowing the synthesis of anti-α-alkyl α-hydroxy β-amino acids. Our procedure involves the intermediate formation of trans-oxazolines, which are alkylated at C-5 with good to high diastereoselectivity and then hydrolysed under mildly acidic conditions, affording in quantitative yield the corresponding hydroxy amides. The starting (R)-3-amino-3-phenylpropanoic acid and (S)-3-aminobutanoic acid were obtained in enantiomerically pure form by selective enzymatic hydrolysis of the corresponding phenylacetylamides with penicillin G acylase.
