Asymmetric Allylic Substitution‐Isomerization for the Modular Synthesis of Axially Chiral N‐Vinylquinazolinones

• DOI: 10.1002/anie.202310320
• Publication Date: 2023-08-16T15:47:47Z
• Authors: Jia‐Yu Zou; Yu‐Ying Yang; Jun Gu; Fei Liu; Zhiwen Ye; Wenbin Yi; Ying He
• Keywords: Atropisomer; Axial Chirality; Axial symmetry

Abstract Axially chiral N ‐substituted quinazolinones are important bioactive molecules, which presented in many synthetic drugs. However, most strategies toward their atroposelective synthesis mainly limited to the axially arylquinazolinone frameworks. The development of modular methods access diverse quinazolinone‐based atropisomers remains scarce and challenging. Herein, we report regio‐ ‐vinylquinazolinones via strategy asymmetric allylic substitution‐isomerization. catalysis system utilized both transition‐metal organocatalysis efficiently afford trisubstituted tetrasubstituted ‐vinylquinazolinone atropisomers, respectively. With meticulous design β‐substituted substrates, Z ‐ E ‐tetrasubstituted were obtained good yields high enantioselectivities.