Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals

被引:266
作者
Loxq, Pauline [1 ,2 ]
Manoury, Eric [1 ,2 ]
Poli, Rinaldo [1 ,2 ,3 ]
Deydier, Eric [1 ,2 ,4 ]
Labande, Agnes [1 ,2 ]
机构
[1] CNRS, Lab Chim Coordinat, F-31077 Toulouse 4, France
[2] Univ Toulouse, UPS, INPT, F-31077 Toulouse 4, France
[3] Inst Univ France, F-75005 Paris, France
[4] IUT A Paul Sabatier, Chim, F-81104 Castres, France
关键词
Axial chirality; Biaryls; Asymmetric catalysis; Transition metals; Atropisomerism; CROSS-COUPLING REACTIONS; SUZUKI-MIYAURA REACTION; ENANTIOSELECTIVE 2+2+2 CYCLOADDITION; N-HETEROCYCLIC CARBENES; CARBON BOND FORMATION; GRIGNARD-REAGENTS; PALLADIUM COMPLEXES; ARYL CHLORIDES; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE ADDITION;
D O I
10.1016/j.ccr.2015.07.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Axially chiral biaryl structures are unique systems encountered in various synthetic compounds such as BINAP and BINOL, polymers, but also in natural products presenting a pharmaceutical interest such as Vancomycin, Steganacin or Korupensamine. The axial chirality of these products, so-called atropisomerism, is induced by the restricted rotation around the aryl-aryl bond. This review will summarize the different strategies imagined by chemists to control such chirality, focusing on asymmetric catalytic processes with transition metals. Only transition metal complexes bearing chiral ligands will be considered and the core of this review will consist of the enantioselective coupling of two achiral substrates. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:131 / 190
页数:60
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