Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11911-11921Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01770
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Funding
- National Program of Sustainability [LO1304, LO1305]
- Palacky University [IGA_PrF_2019_027]
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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 (Delta delta(PM)) than the conventional Mosher's acid.
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