Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral Derivatizing Agent for α-Chiral Primary Amines and Secondary Alcohols To Determine the Absolute Configuration

Autor:	Sandra Benická, Michal Kriegelstein, Adam Přibylka, Antonín Lyčka, David Profous, Tereza Volná, Zdeněk Trávníček, Petr Cankař
Rok vydání:	2019
Předmět:	Atropisomer chemistry.chemical_compound Primary (chemistry) Chemistry Chemical shift Organic Chemistry Absolute configuration Chiral derivatizing agent Racemization Medicinal chemistry Benzoic acid
Zdroj:	The Journal of organic chemistry. 84(18)
ISSN:	1520-6904
Popis:	Racemic 2-(2-trifluoromethyl)-1H-benzo[d]imidazol-1-yl)benzoic acid (TBBA) was synthesized in three steps from 1-fluoro-2-nitrobenzene. Target (P)- and (M)-TBBA atropisomers were stable with a racemization barrier above 30 kcal/mol. As a chiral derivatizing agent, TBBA showed much higher differences in chemical shifts (ΔδPM) than the conventional Mosher's acid.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ea701483fc7d9f0472915898d11a683c https://pubmed.ncbi.nlm.nih.gov/31449414 Zobrazit plný text záznamu