Synthesis of Chiral‐Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions | Zendy

Xia Wang | Zendy; Li Yongsu | Zendy; Zhou Zihong | Zendy; Chen Huixuan | Zendy; Liang Hao | Zendy; Yu Sifan | Zendy; He Xuefeng | Zendy; Zhang Yaqi | Zendy; Pang Jiyan | Zendy; Zhou Zhongyuan | Zendy; Qiu Liqin | Zendy

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Synthesis of Chiral‐Bridged Atropisomeric Monophosphine Ligands with Tunable Dihedral Angles and their Applications in Asymmetric Suzuki–Miyaura Coupling Reactions

Author(s) -

Xia Wang,

Li Yongsu,

Zhou Zihong,

Chen Huixuan,

Liang Hao,

Yu Sifan,

He Xuefeng,

Zhang Yaqi,

Pang Jiyan,

Zhou Zhongyuan,

Qiu Liqin

Publication year - 2017

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.201700020

Subject(s) - chemistry , diastereomer , dihedral angle , annulation , biphenyl , combinatorial chemistry , axial chirality , palladium , coupling reaction , enantioselective synthesis , catalysis , stereochemistry , organic chemistry , molecule , hydrogen bond

Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate‐directed asymmetric annulation reactions. A series of new chiral‐bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′‐biaryl‐2‐phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium‐catalyzed asymmetric Suzuki coupling reactions.

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