Asymmetric Copper(I)-Catalyzed Azide–Alkyne Cycloaddition to Quaternary Oxindoles

Zhou, Feng; Tan, Chen; Tang, Jing; Zhang, Yanyan; Gao, Weiming; Wu, Haihong; Yu, Yihua; Zhou, Jian

doi:10.1021/ja4066656

Cited by 157 publications

(79 citation statements)

References 75 publications

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“…34 To improve the solubility of the copper catalyst in organic solvents other copper(I) salts such as CuOTfC6H6 and [Cu(NCMe)4]PF6 have been successfully used in conjunction with 2,6-lutidine as base. 4 Commercially available sulphurcontaining Cu(I) complex [CuBrSMe2]2 was reported to exhibit good catalytic activity both "on water" 35a (the catalyst is not soluble in H2O) and in organic solvent.…”

Section: Scheme 5 Cui-catalysed Synthesis Of Triazoles In Absence Of mentioning

confidence: 99%

Copper-catalysed azide–alkyne cycloadditions (CuAAC): an update

2015

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The reactions of organic azides and alkynes catalysed by copper species represent the prototypical examples of click chemistry. The so-called CuAAC reaction (copper-catalysed azide-alkyne cycloaddition), discovered in 2002, has been expanded since then to become an excellent tool in organic synthesis. In this contribution the recent results described in the literature since 2010 are reviewed, classified according to the nature of the catalyst precursor: copper(I) or copper(II) salts or complexes, metallic or nano-particulated copper and several solid-supported copper systems.

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Section: Scheme 5 Cui-catalysed Synthesis Of Triazoles In Absence Of mentioning

confidence: 99%

Copper-catalysed azide–alkyne cycloadditions (CuAAC): an update

2015

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“…Chiral copper‐catalyzed azide–alkyne cycloaddition (CuAAC) has been applied in the asymmetric desymmetrization of substrates with two alkyne moieties (Scheme ) 54. Uozumi and co‐workers applied this strategy in the desymmetrization of bis‐alkyne‐containing biaryls rac ‐ 70 55.…”

Section: Dynamic Kinetic Resolution (Dkr)/desymmetrizationmentioning

confidence: 99%

Catalytic Kinetic Resolution of Biaryl Compounds

Sibi

2015

Chemistry A European J

177

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Biaryl compounds with axial chirality are very common in synthetic chemistry, especially in catalysis. Axially chiral biaryls are important due to their biological activities and extensive applications in asymmetric catalysis. Thus the development of efficient enantioselective methods for their synthesis has attracted considerable attention. This Minireview discusses the progress made in catalytic kinetic resolution of biaryl compounds and chronicles significant advances made recently in catalytic kinetic resolution of biaryl scaffolds.

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“…9 This novel approach is only the second report of an asymmetric CuAAC reaction. 10 Treatment of dialkynes such as 7 in the presence of CuCl and Pybox ligand 11 in the unusual solvent 2,5-hexanedione led to enantiomerically enriched chiral quaternary oxindoles bearing a 1,2,3-triazole moiety 9 .…”

Section: Organometallicmentioning

confidence: 99%

Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization

Petersen

2015

Tetrahedron Letters

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The asymmetric desymmetrization of meso or prochiral compounds containing an all-carbon quaternary center is an attractive alternative to classical synthetic approaches aimed at the asymmetric formation of a new C—C bond. This review focuses on nonenzymatic desymmetrizations that utilize transition metal catalysts or organocatalysts to distinguish between enantiotopic groups to generate enantioenriched compounds containing all-carbon quaternary stereocenters.

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Asymmetric Copper(I)-Catalyzed Azide–Alkyne Cycloaddition to Quaternary Oxindoles

Abstract: We report a highly enantioselective Cu(I)-catalyzed azide-alkyne cycloaddition via asymmetric desymmetrization of oxindole-based 1,6-heptadiynes, which furnishes quaternary oxindoles bearing a 1,2,3-triazole-containing moiety with 84-98% ee.

Cited by 157 publications

References 75 publications

Copper-catalysed azide–alkyne cycloadditions (CuAAC): an update

Copper-catalysed azide–alkyne cycloadditions (CuAAC): an update

Catalytic Kinetic Resolution of Biaryl Compounds

Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization

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