Construction of C−C Axial Chirality via Asymmetric Carbene Insertion into Arene C−H Bonds. Issue 49 (3rd November 2021)

• Record Type: Journal Article
• Authors: Li, Ziyong; Chen, Ying; Wang, Chuang; Xu, Guangyang; Shao, Ying; Zhang, Xinhao; Tang, Shengbiao; Sun, Jiangtao
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 49(2021)
• Page Start: 25714
• Page End: 25718
• Publication Date: 2021-11-03
• Subjects: asymmetric catalysis -- atropisomer -- axial chirality -- carbene -- C–H insertion; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202110430
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp 2 )−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands. Abstract : By using diazonaphthoquinones and anilines as key reagents and through a point‐to‐axis chiral transfer strategy, the atroposelective synthesis via asymmetric C(sp 2 )−H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1).