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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.