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

Andrea Mazzanti | Zendy; Maria Boffa | Zendy; Emanuela Marotta | Zendy; Michele Mancinelli | Zendy

Open Access

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

Author(s) -

Andrea Mazzanti,

Maria Boffa,

Emanuela Marotta,

Michele Mancinelli

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b01550

Subject(s) - atropisomer , racemization , chemistry , aryl , circular dichroism , chirality (physics) , axial chirality , single bond , absolute configuration , enantioselective synthesis , crystallography , stereochemistry , organic chemistry , catalysis , alkyl , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark

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.

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