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Lipoic acid is a short\u2010chain fatty acid containing an asymmetric carbon at five bonds of distance to the organic function. Herein, we developed a nuclear magnetic resonance protocol to access the chiral recognition of lipoic acid in a simple and rapid procedure employing cinchonidine as a cheap chiral solvation agent in deuterated chloroform. To optimize this method, a statistical design of the experimental model was performed to produce a clear understanding of the optimal concentration, temperature, and molar ratio parameters. Based on the obtained spectra, the cinchonidine H<jats:sub>8<\/jats:sub>\u2010H<jats:sub>9<\/jats:sub> scalar coupling indicated a conformational preference in the chiral discrimination procedure. Density functional theory calculations established a proximity between the asymmetric center of lipoic acid and the aromatic moiety of cinchonidine, clarifying possible conformations in this ion\u2010pair interaction. The described protocol demonstrates how far is far enough to chiral discrimination using a chiral solvation agent, expanding the method to compounds that contain a remote stereocenter.<\/jats:p>","DOI":"10.1002\/chir.23514","type":"journal-article","created":{"date-parts":[[2022,11,7]],"date-time":"2022-11-07T04:24:20Z","timestamp":1667795060000},"page":"40-48","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["NMR chiral recognition of lipoic acid by cinchonidine CSA: A stereocenter beyond the organic function"],"prefix":"10.1002","volume":"35","author":[{"given":"Talia Behnen","family":"Marta","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de S\u00edntese Org\u00e2nica Limpa \u2010 LASOL Universidade Federal de Pelotas \u2010 UFPel  Pelotas Rio Grande do Sul Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Augusto Cardozo","family":"Argondizzo","sequence":"additional","affiliation":[{"name":"Grupo de Cat\u00e1lise e Estudos Te\u00f3ricos Universidade Federal de Pelotas \u2013 UFPel  Pelotas Rio Grande do Sul Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robson","family":"da Silva Oliboni","sequence":"additional","affiliation":[{"name":"Grupo de Cat\u00e1lise e Estudos Te\u00f3ricos Universidade Federal de Pelotas \u2013 UFPel  Pelotas Rio Grande do Sul Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7606-564X","authenticated-orcid":false,"given":"M\u00e1rcio Santos","family":"Silva","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de S\u00edntese Org\u00e2nica Limpa \u2010 LASOL Universidade Federal de Pelotas \u2010 UFPel  Pelotas Rio Grande do Sul 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