Enantioselective Synthesis of Axially Chiral 1‐Arylisoquinolines by Rhodium‐Catalyzed [2+2+2] Cycloaddition

Sakiyama, Norifumi; Hojo, Daiki; Noguchi, Keiichi; Tanaka, Ken

doi:10.1002/chem.201003134

Cited by 50 publications

(17 citation statements)

References 85 publications

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“…Scheme 6.28 -Asymmetric aerobic oxidative polymerization of 2,3-dihydroxynaphthalene using chiral vanadium complexes obtained from tartaric acid salts [204]. M a n u s c r i p t Scheme 7.20 -Rhodium-catalyzed synthesis of axially chiral 1-arylisoquinolines [236]. M a n u s c r i p t 74 88 11 CO 2 iPr 141-G3 (0.1) 77 90 Table 7.3 -Enantioselective synthesis of ynamides [238].…”

Section: -Direct C-h Functionalizationmentioning

confidence: 99%

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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Section: -Direct C-h Functionalizationmentioning

confidence: 99%

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

Loxq

Manoury

Poli

et al. 2016

Coordination Chemistry Reviews

295

View full text Add to dashboard Cite

show abstract

“…Methods that allow to directly obtain unsymmetrical ligands with different degree of substitution in a selective reaction are thus especially valuable. By considering a de novo ring construction approach, Tanaka reported a highly enantioselective [2+2+2]-cycloaddition of alkynyl phosphine oxides (15) and symmetrical 1,6-diynes (14) (Scheme 4). 15 The reaction is catalyzed by a rhodium/H8-BINAP complex and proceeds under mild conditions, affording the target QUINAP-type phosphine oxide (16) in high yields and selectivity.…”

Section: Scheme 3 Atroposelective Benzidine Rearrangementmentioning

confidence: 99%

“…By considering a de novo ring construction approach, Tanaka reported a highly enantioselective [2+2+2]-cycloaddition of alkynyl phosphine oxides (15) and symmetrical 1,6-diynes (14) (Scheme 4). 15 The reaction is catalyzed by a rhodium/H8-BINAP complex and proceeds under mild conditions, affording the target QUINAP-type phosphine oxide (16) in high yields and selectivity. Subsequent reduction of the phosphine oxides affords the QUINAP-type ligand, as shown by the reaction of (17) with HSiCl3, which yields the target P,N-ligand (18) without affecting the enantiomeric purity.…”

Section: Scheme 3 Atroposelective Benzidine Rearrangementmentioning

confidence: 99%

Catalyst-Controlled Stereoselective Synthesis of Atropisomers

2018

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Owing to their favorable molecular topology, atropisomers represent particularly valuable chiral scaffolds for numerous applications throughout academic research and industry. Nevertheless, whereas various well-established catalyst-controlled methodologies allow addressing stereocenter configuration, efficient procedures to prepare axially chiral compounds in high isomeric purity are still scarce. Complementary to the comprehensive reviews in the area, this perspective article features representative advances for the catalyst-stereocontrolled synthesis of atropisomeric scaffolds. With a focus on axially chiral motifs frequently utilized in catalysis or medicinal chemistry, selected recent examples encompassing unique stereoselective transition metal, hydrogen bond, ion pairing, chiral phosphoric acid, and amine catalysis are highlighted.

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“…The Tanaka group then developed an enantioselective synthesis of the C 2 symmetric tetra-ortho-substituted axially chiral biaryls 62 using [Rh(cod) 2 ]BF 4 (5 mol%) as the metal precursor and (S)-Segphos (5 mol%) as a chiral ligand (Scheme 19). 54 Similar protocols were described for the synthesis of many chiral compounds bearing phthalan moieties: biaryl diphosphines, 55 diphosphonates and dicarboxylates, 56 N,O-biaryls, 57 P-stereogenic alkynylphosphine oxides, 58 as well as axially chiral N,N-dialkylbenzamides, 59 1-arylisoquinolines, 60 and hydroxy carboxylic acid derivatives. 61…”

Section: Scheme 18 Axially Chiral Anilides Via Enantioselective Rh-camentioning

confidence: 99%

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

Albano

Aronica

2018

Synthesis

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Oxygen and nitrogen heterocycles are present in a vast number of natural substrates and biologically active molecules. In particular, phthalan and isoindoline subunits are found in many classes of products such as antibiotics, antioxidants, antimycotics, pigments, and fluorophores. Therefore several procedures dedicated to the construction of these heterocycles have been developed. In this review, a detailed analysis of the literature data regarding the synthesis of these nuclei via cyclization reactions is reported.1 Introduction2 Phthalans2.1 Oxa-Pictet–Spengler Reaction2.2 Garratt–Braverman Cyclization2.3 Diels–Alder and Related Reactions2.4 [2+2+2] Cyclotrimerization of Alkynes2.5 Cycloetherification of ortho-Substituted Aromatics2.6 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions3 Isoindolines3.1 Amination of Dihalides3.2 Intramolecular Hydroamination3.3 Diels–Alder and Related Reactions3.4 [2+2+2] Cycloaddition Reactions3.5 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions4 Conclusions

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Enantioselective Synthesis of Axially Chiral 1‐Arylisoquinolines by Rhodium‐Catalyzed [2+2+2] Cycloaddition

Cited by 50 publications

References 85 publications

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

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

Catalyst-Controlled Stereoselective Synthesis of Atropisomers

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

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Enantioselective Synthesis of Axially Chiral 1‐Arylisoquinolines by Rhodium‐Catalyzed [2+2+2] Cycloaddition

Cited by 50 publications

References 85 publications

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

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

Catalyst-Controlled Stereoselective Synthesis of Atropisomers

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

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Cyclization Reactions for the Synthesis of Phthalans and Isoindolines