Asymmetric Assembly of Aromatic Rings To Produce Tetra‐<i>ortho</i>‐Substituted Axially Chiral Biaryl Phosphorus Compounds

Nishida, Goushi; Noguchi, Keiichi; Hirano, Masao; Tanaka, Ken

doi:10.1002/anie.200700064

Cited by 175 publications

(42 citation statements)

References 48 publications

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“…The utility of these ligands has resulted in the introduction of structurally related variants by others [89][90][91][92][93][94][95][96][97][98][99][100][101][102][103][104][105] and has spawned innovative alternative synthetic routes by Diels-Alder reaction [96,106] and formal rhodiumcatalyzed [2+2+2] cycloaddition. [107,108] …”

Section: Introductionmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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Palladium-catalyzed amination of aryl halides has undergone rapid development in the last 12 years. This has been largely driven by implementation of new classes of ligands. Biaryl phosphines have proven to provide especially active catalysts in this context. This review discusses the applications that these catalysts have found in C-N cross-coupling in heterocycle synthesis, pharmaceuticals, materials science and natural product synthesis.

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Section: Introductionmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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“…[3] Considerable effort has been devoted to the search for efficient routes on the synthesis of chiral biaryl backbones,a nd relatively practical approaches have already been developed, including aryl-aryl couplings, [4] functionalization of racemic or prochiral biaryls (desymmetrization, kinetic resolution, etc. ), [5] de novo construction of one or two aryl ring(s), [6] and rearomatization of chiral non-aromatic bicyclicp recursors. [7] In sharp contrast, the enantioselective construction of atropisomeric heteroaryl structures still constitutes adaunting challenge of modern organic synthesis.…”

mentioning

confidence: 99%

Organocatalytic Atroposelective Intramolecular [4+2] Cycloaddition: Synthesis of Axially Chiral Heterobiaryls

Liu

et al. 2018

Angewandte Chemie

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The enantioselective construction of axially chiral aryl-naphthopyran skeletons was realized by organocatalytic atroposelective intramolecular [4+ +2] cycloaddition of in situ generated vinylidene ortho-quinone methides,from 2-ethynylphenol derivatives,w ith alkynes.T hrough this method, the heteroatropisomers were obtained with excellent yields and enantioselectivities.M oreover,aspeculative model of the stereochemical outcome is proposed based on preliminary mechanistic studies.T he products having various functional groups can be easily transformed into valuable intermediates as either potential ligands or organocatalysts. Scheme 1. Previous work and our strategy.

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“…Differently substituted internal alkynes were used in association with dialkyl acetylenedicarboxylates and the products were obtained with high enantioselectivities, ranging from 84% to 96% ee, and reasonable to good yields [221]. The same rhodium salt/chiral ligand combination allowed them to obtain synthetically challenging axially chiral, tetra-ortho-substituted biaryl phosphorus compounds that could be of great interest as ligands in other types of asymmetric catalyses (Scheme 7.12) [222]. Such structures could not be synthesized via asymmetric Suzuki-Miyaura cross-coupling, the latter being limited to less sterically challenging tri-orthosubstituted biaryl phosphonates [51].…”

Section: Co Catalystsmentioning

confidence: 98%

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

Loxq

Manoury

Poli

et al. 2016

Coordination Chemistry Reviews

295

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Please cite this article as: P. Loxq, E. Manoury, R. Poli, E. Deydier, A. Labande, Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals, Coordination Chemistry Reviews (2015), http://dx. AbstractAxially 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. Highlights 1. A review on the synthesis of axially chiral biaryls by asymmetric catalysis 2. Exhaustive description of chiral ligands used in the palladium-catalyzed SuzukiMiyaura cross-coupling reaction 3. Emerging reactions such as asymmetric direct C-H functionalization are presented 4. Asymmetric [2+2+2] cycloadditions catalyzed by group 9 transition metals are included

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Asymmetric Assembly of Aromatic Rings To Produce Tetra‐ortho‐Substituted Axially Chiral Biaryl Phosphorus Compounds

Cited by 175 publications

References 48 publications

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

Organocatalytic Atroposelective Intramolecular [4+2] Cycloaddition: Synthesis of Axially Chiral Heterobiaryls

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

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