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English6-Aryl-5,6-dihydrodibenzo[c,e][1,2]azaborinines display restricted rotation at the boron-carbon aryl bond, yielding conformational isomers or atropisomers. The stereodynamic processes were monitored by variable-temperature NMR (D-NMR), dynamic enantioselective HPLC (D-HPLC), or kinetic racemization measurements. The absolute configuration of stable atropisomers (compound 1d, ΔGrac = 26.0 kcal·mol-1) was determined by TD-DFT simulation of the electronic circular dichroism (ECD) spectra. The racemization energy of 1d is more than 12 kcal·mol-1 smaller than its isostere 9-(2-methylnaphthalen-1-yl)phenanthrene.
| Titolo: | Axial Chirality at the Boron-Carbon Bond: Synthesis, Stereodynamic Analysis, and Atropisomeric Resolution of 6-Aryl-5,6-dihydrodibenzo[ c,e][1,2]azaborinines |
| Autore/i: | Mazzanti A.; Boffa M.; Marotta E.; Mancinelli M. |
| Autore/i Unibo: | |
| Anno: | 2019 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.joc.9b01550 |
| Abstract: | 6-Aryl-5,6-dihydrodibenzo[c,e][1,2]azaborinines display restricted rotation at the boron-carbon aryl bond, yielding conformational isomers or atropisomers. The stereodynamic processes were monitored by variable-temperature NMR (D-NMR), dynamic enantioselective HPLC (D-HPLC), or kinetic racemization measurements. The absolute configuration of stable atropisomers (compound 1d, ΔGrac = 26.0 kcal·mol-1) was determined by TD-DFT simulation of the electronic circular dichroism (ECD) spectra. The racemization energy of 1d is more than 12 kcal·mol-1 smaller than its isostere 9-(2-methylnaphthalen-1-yl)phenanthrene. |
| Data stato definitivo: | 2020-02-24T21:52:37Z |
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