Atroposelective Synthesis of C-N Axially Chiral Biaryls via Catalytic C-H Functionalization at a Remote Site
Jinlei Wang1,2, Yunfei Yao2, Fen Wang2
1School of Chemistry and Chemical Engineering, Zhoukou Normal University, Zhoukou, Henan 466001, China.
Abstract:
Construction of axial chirality via distal functionalization consists of a significant challenge. Reported herein is the atroposelective synthesis of C-N axially chiral biaryls based on C-H bond activation at a site that is three bonds away from the axis atom. Under rhodium catalysis, naphthalimides bearing a bulky N-aryl group undergo carbonyl group-assisted C-H bond activation en route to alkynylation or alkenylation via desymmetrization or parallel kinetic resolution. Mechanistic studies indicate that C-H bond activation is likely enantiodetermining.
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