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Updated: Jan 23, 2026

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Published on: June 23, 2019
Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination
Xihao Chang1, Qinglin Zhang1, Chang Guo1
1Hefei National Laboratory for Physical Sciences at the Microscale , University of Science and Technology of China , Hefei 230026 , China.
Abstract:
Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselective amination reactions of O-arenes provides access to nonsymmetric 2'-amino[1,1'-binaphthalen]-2-ol (i.e., NOBIN-type) and [1,1'-binaphthalene]-2,2'-diamine (i.e., BINAM-type) derivatives. This transition metal-free strategy provides a powerful way to access a wide range of advanced highly functionalized enantioenriched anilines.
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