Chiral Lewis Acid Catalyzed Reactions of α‐Diazoester Derivatives: Construction of Dimeric Polycyclic Compounds

Tan, Fei; Liu, Xiaohua; Wang, Yan; Dong, Shujuan; Han, Yuling; Feng, Xiaoming

doi:10.1002/ange.201810030

Cited by 10 publications

(1 citation statement)

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“…[ 37d ] Chiral N , N '‐dioxide‐metal complexes were further applied in the asymmetric cascade reactions of α ‐diazoester derivatives (Scheme 10c). [ 38 ]…”

Section: Representative Applicationsmentioning

confidence: 99%

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Wang

2021

Chin. J. Chem.

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Feng ligand | N,N'-Dioxide | O ligands | Asymmetric catalysis | Lewis acids Catalysts and ligands possessing the great ability to tolerate over a wide range of mechanistically unrelated reactions are remarked as "privileged", which are rather scarce but extremely meaningful in asymmetric catalysis. Feng and co-workers have developed a library of conformationally flexible, C 2-symmetric N,N'-dioxide amide compounds with original design and featured structure (named as Feng ligand now). They were initially reported as chiral organocatalysts in 2005 and have been further developed as a new class of privileged chiral ligands since 2006. Tremendous success, including versatile coordination chemistry with plenty of metal sources (main-group metals, transition metals, and rare-earth metals), a truly broad scope of asymmetric reactions (more than 50 types), diverse areas of catalysis (organocatalysis, Lewis-acid catalysis, bimetallic relay catalysis, and photocatalysis), numerous synthetic applications of bioactive compounds, has been achieved using Feng N,N'-dioxide. Besides, they demonstrate that chiral ligands with conformationally flexible property can offer excellent chiral environment as well, which challenges the conventional idea preferring rigid structures in the design of chiral ligands. Herein, we briefly introduced the discovery of Feng ligand and the millstones during the development. We also covered the successful applications of Feng ligand by other scientists as well as novel chiral ligands inspired by them. Contents 1. Introduction 969 2. Initial Discovery 970 3. Representative Applications 971 3.1. Classical asymmetric reactions 971 3.2. Novel asymmetric reactions 975 4. Studies by Other Groups 977 4.1. Reactions using Feng ligand 977 4.2. Novel chiral ligands inspired by Feng ligand 980 5. Conclusions 980

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“…[ 37d ] Chiral N , N '‐dioxide‐metal complexes were further applied in the asymmetric cascade reactions of α ‐diazoester derivatives (Scheme 10c). [ 38 ]…”

Section: Representative Applicationsmentioning

confidence: 99%

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Wang

2021

Chin. J. Chem.

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Xiaohua Liu

2020

Angewandte Chemie

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Meine liebste Tageszeit ist, wenn ich durch den Garten spaziere. Meine Lieblingsgetränke sind grüner Te eund Kaffee. Meine liebste Art Urlaub zu machen ist bei meiner Familie. Wenn ich ein Jahr bezahlten Urlaub hätte,würde ich um die Welt reisen. Mein Lieblingsmaler ist Baishi Qi, ein Meister der traditionellen chinesischen Malerei. Was ich an meinen Freunden am meisten schätze,ist, dass sie mich unterstützen und aufmuntern. Das Wichtigste,d as ich von meinen Studenten gelernt habe,s ind Leidenschaft und Beharrlichkeit. Meine Wissenschafts"helden" sind Pasteur,E instein, Pauling,M endelejew,W oodward und Stork. Meine Lieblingsreaktionen sind Umlagerungen:G ruppen verschieben sich und verbinden sich neu. Mit achtzehn wollte ich Architektin werden, heute bin ich Baumeisterin fürMoleküle. Ich warte auf die Entwicklung von Ausrüstung,ume ine katalytische Reaktion real zu filmen. Die grçßten Herausforderungen fürW issenschaftler sind Neugier behalten und Stçrungen meiden. Chemie macht Spaß, weil sie nützlich, kreativ und logisch ist-und Substanz hat. Junge Leute sollten Chemie studieren, weil Chemie wichtig füru nser Leben ist, und weil chemische Experimente wahre Ergebnisse liefern.

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Copper‐Nitrene‐Catalyzed Desymmetric Oxaziridination/1,2‐Alkyl Rearrangement of 1,3‐Diketones toward Bicyclic Lactams

et al. 2021

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Although copper-nitrene has been extensively studied as a versatile active species in various transformations, asymmetric reactions involving copper-nitrene have been limited to the aziridination of olefins. Herein, we report the novel copper-nitrene-catalyzed desymmetric oxaziridination reaction of cyclic diketones with alkyl azides and the subsequent rearrangement of the resulting highly active intermediate, which produces a synthetically challenging chiral bicyclic lactam containing a quaternary carbon center. This procedure not only enriches the copper-nitrene-catalyzed asymmetric reactions, but also provides an alternative strategy to address the inherent challenges of catalytic asymmetric Schmidt reactions. This unique reaction could inspire the investigation of novel copper-nitrene-catalyzed asymmetric transformations and their reaction mechanisms.Scheme 1. The outline of Cu-catalyzed asymmetric reactions involving nitrenoid intermediates.

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Chiral Lewis Acid Catalyzed Reactions of α‐Diazoester Derivatives: Construction of Dimeric Polycyclic Compounds

Cited by 10 publications

References 40 publications

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Feng Ligand: Privileged Chiral Ligand in Asymmetric Catalysis

Xiaohua Liu

Copper‐Nitrene‐Catalyzed Desymmetric Oxaziridination/1,2‐Alkyl Rearrangement of 1,3‐Diketones toward Bicyclic Lactams

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