A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline

Add time:08/06/2019    Source:sciencedirect.com

Enantiopure methyl esters of 1-alkyl-5-oxo-3-pyrrolidinecarboxylic acids were obtained by enzymatic resolution of the corresponding chiral racemic mixtures. A particularly favourable interaction, also supported by molecular mechanics calculations, was observed between the 1-benzyl derivative and α-chymotrypsin, for which the enantiomeric ratio, E, exceeded 200. The absolute configurations of the lactams were determined by means of CD spectroscopy. From the resulting enantiomerically pure (99% e.e.) (S)-(+)-1-benzyl-3-pyrrolidinecarboxylic acid and methyl (R)-(−)-1-benzyl-3-pyrrolidinecarboxylate, the methyl esters of (+) and (−)-β-proline were synthesised in 99% e.e. and 18 and 22% overall yield, respectively.

We also recommend Trading Suppliers and Manufacturers of METHYL N-BENZYL-3-PYRROLIDINECARBOXYLATE (cas 17012-21-4). Pls Click Website Link as below: cas 17012-21-4 suppliers

Prev:Carbon and hydrogen isotope fractionation of phthalate esters during degradation by sulfate and hydroxyl radicals
Next:A novel, potent, and orally active VLA-4 antagonist with good aqueous solubility: trans-4-[1-[[2-(5-Fluoro-2-methylphenylamino)-7-fluoro-6-benzoxazolyl]acetyl]-(5S)-[methoxy(methyl)amino]methyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid)