Asymmetric Azide–Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles

Zhang, Xue; Li, Shunian; Yu, Wenjing; Xie, Yufang; Tung, Chen‐Ho; Xu, Zhenghu

doi:10.1021/jacs.2c02563

Cited by 57 publications

(26 citation statements)

References 91 publications

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“…Upon further investigation, they found that the yield dramatically decreases with an increase in the steric hindrance. and co-workers 130 reported a first atroposelective approach for the synthesis of axially chiral aryl triazole 258 from internal alkynes 257 and azides 2 using Ir(I)/squaramide (O) 259 and DCE/EtOH (5:1) at 25 °C (Scheme 64). The optimum asymmetric induction was achieved with quinidine squaramide (O) and Ir(I).…”

Section: [Ir(cod)cl] 2 -Catalyzed Synthesismentioning

confidence: 99%

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Vala

Patel

2022

ACS Omega

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1,2,3-Triazole scaffolds are not obtained in nature, but they are still intensely investigated by synthetic chemists in various fields due to their excellent properties and green synthetic routes. This review will provide a library of all synthetic routes used in the past 21 years to synthesize 1,2,3-triazoles and their derivatives using various metal catalysts (such as Cu, Ni, Ru, Ir, Rh, Pd, Au, Ag, Zn, and Sm), organocatalysts, metal-free as well as solvent- and catalyst-free neat syntheses, along with their mechanistic cycles, recyclability studies, solvent systems, and reaction condition effects on regioselectivity. Constant developments indicate that 1,2,3-triazoles will help lead to future organic synthesis and are useful for creating molecular libraries of various functionalized 1,2,3-triazoles.

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Section: [Ir(cod)cl] 2 -Catalyzed Synthesismentioning

confidence: 99%

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Vala

Patel

2022

ACS Omega

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“…The atroposelective azide−alkyne cycloaddition to offer axially chiral aryl triazoles was recently disclosed by Xu and co-workers via an Ir(I)/squaramide cooperative catalytic procedure ( Scheme 4 ) [ 65 ]. It was found that the metal catalyst, reaction solvent, and temperature all play a key role in the increase in enantioselectivity.…”

Section: The De Novo Synthesis Of Axially Chiral Heterobiaryl Scaffol...mentioning

confidence: 99%

Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds

et al. 2022

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Axially chiral heterobiaryl frameworks are privileged structures in many natural products, pharmaceutically active molecules, and chiral ligands. Therefore, a variety of approaches for constructing these skeletons have been developed. Among them, de novo synthesis, due to its highly convergent and superior atom economy, serves as a promising strategy to access these challenging scaffolds including C–N, C-C, and N-N chiral axes. So far, several elegant reviews on the synthesis of axially chiral heterobiaryl skeletons have been disclosed, however, atroposelective construction of the heterobiaryl subunits by de novo synthesis was rarely covered. Herein, we summarized the recent advances in the catalytic asymmetric synthesis of the axially chiral heterobiaryl scaffold via de novo synthetic strategies. The related mechanism, scope, and applications were also included.

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“…We initially used the internal alkyne ( 1 a ) and sulfonium ylide ( 2 a ) as model substrates (Table 1). Following our earlier research, [13] Ir/quinidine squaramide ( O ) was used as the catalyst. An axial chiral arylfuran product was expected through a [3+2] cycloaddition reaction with the triple bond and the release of dimethyl sulfide (DMS).…”

Section: Figurementioning

confidence: 99%

Synthesis of Benzofurans from Sulfur Ylides and ortho‐Hydroxy‐Functionalized Alkynes

Tung

2022

Adv Synth Catal

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The synthesis of benzofurans from readily accessible sulfur ylides and ortho‐hydroxy aryl alkynes is reported. The transformation proceeds through an isomerization/nucleophilic addition/cyclization/aromatization cascade. The substrate scope is very general with respect to both reactants and the products are afforded in 43–94% yield under conditions which are catalyst‐free and additive‐free.

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Asymmetric Azide–Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles

Cited by 57 publications

References 91 publications

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds

Synthesis of Benzofurans from Sulfur Ylides and ortho‐Hydroxy‐Functionalized Alkynes

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