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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 , Δ G  ⧧  rac = 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.

journal of organic chemistry

Axial Chirality at the Boron–Carbon Bond: Synthesis, Stereodynamic Analysis, and Atropisomeric Resolution of 6-Aryl-5,6-dihydrodibenzo[<i>c,e</i>][1,2]azaborinines

Axial Chirality at the Boron–Carbon Bond: Synthesis, Stereodynamic Analysis, and Atropisomeric Resolution of 6-Aryl-5,6-dihydrodibenzo[c,e][1,2]azaborinines