Synthesis of Isotopic Atropisomers Based on 12 C/ 13 C Discrimination.

Authors :: Senda R
Watanabe Y
Miwa S
Sato A
Kitagawa O
Source :: The Journal of organic chemistry [J Org Chem] 2023 Jul 07; Vol. 88 (13), pp. 9579-9583. Date of Electronic Publication: 2023 Jun 10.
Publication Year :: 2023
Abstract: Quinazolin-4-one derivatives possessing an isotopic atropisomerism (isotopic N-C axial chirality) based on ortho - <superscript>12</superscript> CH <subscript>3</subscript> / <superscript>13</superscript> CH <subscript>3</subscript> discrimination were prepared. The diastereomeric quinazolin-4-ones bearing an asymmetric carbon as well as an isotopic atropisomerism were clearly discriminated by <superscript>1</superscript> H and <superscript>13</superscript> C NMR spectra and revealed to possess high rotational stability and stereochemical purity.