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Assignment of absolute configuration of chiral carboxylic acids via exciton‐coupled CD treatment: 4‐phenylthioproline as a case study
Author(s) -
Di Bari Lorenzo,
Mannucci Serena,
Pescitelli Gennaro,
Salvadori Piero
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10086
Subject(s) - chemistry , absolute configuration , exciton , chirality (physics) , absolute (philosophy) , computational chemistry , stereochemistry , chiral symmetry , condensed matter physics , quantum mechanics , physics , quark , nambu–jona lasinio model , philosophy , epistemology
Abstract 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, (−)‐(2 S ,4 S )‐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 1 H‐NMR NOESY and semiempirical PM3 computational methods, and quantitative CD calculations were necessary to substantiate the assignment based on a weak experimental couplet. Chirality 14:611–617, 2002. © 2002 Wiley‐Liss, Inc.