Assignment of absolute configuration of chiral carboxylic acids via exciton‐coupled CD treatment: 4‐phenylthioproline as a case study | Zendy

Di Bari Lorenzo | Zendy; Mannucci Serena | Zendy; Pescitelli Gennaro | Zendy; Salvadori Piero | Zendy

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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

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.

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