The 4-hydroxybenzoate chromophore was used as an exciton reporter group for the assignment of the absolute configuration of a chiral carboxylic acid of pharmaceutical interest, (-)-(2S,4S)-4-phenylthioproline, precursor of the ACE-inhibitor zofenopril. The nondegenerate coupling with the preexisting phenylthio chromophore was observed. A detailed conformational analysis, accomplished by means of H-1-NMR NOESY and semiempirical PM3 computational methods, and quantitative CD calculations were necessary to substantiate the assignment based on a weak experimental couplet.
|Autori:||DI BARI L; MANNUCCI S.; PESCITELLI G.; SALVADORI P.|
|Titolo:||Assignment of absolute configuration of chiral carboxylic acids via exciton-coupled CD treatment: 4-phenylthioproline as a case study|
|Anno del prodotto:||2002|
|Digital Object Identifier (DOI):||10.1002/chir.10086|
|Appare nelle tipologie:||1.1 Articolo in rivista|