Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide–Alkyne Cycloaddition

Alexander, Juliana R.; Ott, Amy A.; Liu, En Chih; Topczewski, Joseph J.

doi:10.1021/acs.orglett.9b01556

Cited by 28 publications

(13 citation statements)

References 40 publications

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“…Disubstituted 1,2,3-triazoles are most frequently reported as 1,4disubstiuted 1,2,3-triazoles (12) and somewhat less frequently as regio-isomeric 1,5disubstituted 1,2,3-triazoles (13). Such triazoles have found wide-ranging application beyond serving as linking motifs, displaying intra-and intermolecular interactions resulting in a myriad of functional and scaffolding applications in supramolecular, [23][24][25][26][27][28][29][30][31][32][33][34] coordination, [35][36][37] medicinal, 38,39 drug discovery, 40 sensor 41,42 and catalytic [43][44][45][46][47][48][49][50] chemistries. These triazoles are stable at elevated temperatures and under biological conditions rendering them amenable to development for applications in materials 51,52 and chemical biology.…”

Section: Figure 1 Selected Examples Of Atropisomeric Compounds Upper:...mentioning

confidence: 99%

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

et al. 2022

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The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.

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Section: Figure 1 Selected Examples Of Atropisomeric Compounds Upper:...mentioning

confidence: 99%

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

et al. 2022

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Section: Figure 1 Selected Examples Of Atropisomeric Compounds Upper: Natural Products Marinopyrrole a (1); Gossypolmentioning

confidence: 99%

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Meloni

Brittain

Male

et al. 2021

Preprint

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The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3-triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.

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“…当转化率为 36%时, 能以 84∶16 的 dr 值及 90%的 ee 值得到目标化合物 85, 显示能通过不对称 CuAAC 反应构建两个手性中心(Scheme 14c) [33] . 2019 年 Topczewski 等 [34]…”

Section: 去对称化unclassified

Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction

Cai¹,

Zhou²,

Zhou³

2020

Chin. J. Org. Chem.

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As one of the most important click reactions, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) has found widespread applications. Nevertheless, the exploitation of enantioselective CuAAC remains largely undeveloped. Although the reaction itself does not generate chiral elements, the enantioselective CuAAC can be realized via the desymmetrization of prochiral dialkynes or diazides, as well as the kinetic resolution of racemic azides or terminal alkynes. Notably, enantioselective CuAAC provides efficient access to structurally diverse enantioenriched compounds featuring an azide, terminal alkyne or 1,4-disubstituted 1,2,3-triazoles, which are valuable structural units in organic synthesis or medicinal chemistry. Since the first highly enantioselective CuAAC reaction via desymmetrization of prochiral diynes was reported in 2013, substantial progress has been made in this research area. To date, enantioselective CuAAC has been successfully applied to the construction of central chirality, axial chirality and planar chirality. The recent exciting achievements are summarized, the challenges in this context are briefly discussed, and the synthetic opportunities for future development are outlined.

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Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide–Alkyne Cycloaddition

Cited by 28 publications

References 40 publications

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction

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