Asymmetric Azide–Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles

• DOI: 10.1021/jacs.2c02563
• Publication Date: 2022-04-04T17:50:45Z
• Authors: Xue Zhang; Shunian Li; Wenjing Yu; Yufang Xie; Chen-Ho Tung; Zhenghu Xu
• Keywords: Squaramide; Cinchona

An Ir(I)/squaramide cooperative catalytic strategy for atroposelective synthesis of axially chiral aryltriazoles has been developed the first time. Diverse structurally novel aryltriazole skeletons that cannot be accessed by traditional click reactions were synthesized in good yields with excellent enantioselectivity. Both enantiomers easily obtained from a pair diastereoisomeric natural quinidine- and quinine-derived squaramides. A significant coordination activation, but no self-quenching phenomenon was observed this metal/organo system.