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Cascade Chan‐Lam C−O Coupling/[3,3]‐Rearrangement of Arylhydroxylamines with Arylboronic Acids Toward NOBIN Analogues
Author(s) -
Wang Min,
Liu Yue,
Wang Liying,
Lu Haifeng,
Feng Lei,
Gao Hongyin
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001570
Subject(s) - chemistry , cascade , kinetic resolution , stereochemistry , acylation , sigmatropic reaction , medicinal chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , organic chemistry , chromatography
Herein, we developed a copper‐mediated Chan‐Lam type O ‐arylation of arylhydroxylamines with arylboronic acids to generate transient N,O‐ diarylhydroxylamines that could rapidly undergo cascade [3,3]‐sigmatropic rearrangement and rearomatization to afford NOBIN (2‐amino‐2′‐hydroxy‐1,1′‐binaphthyl) analogues under mild conditions. The newly synthesized racemic biaryl products can be further resolved by a chiral DMAP‐catalyzed O ‐acylation/kinetic resolution protocol.