Cascade Chan‐Lam C−O Coupling/[3,3]‐Rearrangement of Arylhydroxylamines with Arylboronic Acids Toward NOBIN Analogues | Zendy

Wang Min | Zendy; Liu Yue | Zendy; Wang Liying | Zendy; Lu Haifeng | Zendy; Feng Lei | Zendy; Gao Hongyin | Zendy

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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.

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