Enolate–Azide [3 + 2]-Cycloaddition Reaction Suitable for DNA-Encoded Library Synthesis DOI

Kangyin Pan,

Ying Yao, Yiyuan Zhang

et al.

Bioconjugate Chemistry, Journal Year: 2023, Volume and Issue: 34(8), P. 1459 - 1466

Published: July 14, 2023

The DNA-encoded chemical library (DEL) is a powerful hit selection technique in either basic science or innovative drug discovery. With the aim to circumvent issue concerning DNA barcode damage conventional on-DNA copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC), we have successfully developed first DNA-compatible enolate–azide [3 + 2] reaction. merits of this DEL chemistry include metal-free and high fidelity, conversions easy operation, broad substrate scope, ready access highly substituted 1,4,5-trisubstituted triazoles. Thus, it will not only further enrich toolbox but also great potential practical synthesis.

Language: Английский

Mask and Release Strategy‐Enabled Diversity‐Oriented Synthesis for DNA‐Encoded Library DOI Creative Commons
Silin Zhang,

Haiman Zhang,

Xiawen Liu

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 11(6)

Published: Dec. 3, 2023

Abstract An ideal DNA‐encoded library (DEL) selection requires the to consist of diverse core skeletons and cover chemical space as much possible. However, lack efficient on‐DNA synthetic approaches toward has greatly restricted diversity DEL. To mitigate this issue, work disclosed a “Mask & Release” strategy streamline challenging skeleton synthesis. N ‐phenoxyacetamide is used masked phenol versatile directing group mediate diversified DNA‐compatible C‐H functionalization, introducing 1st‐dimensional at defined site, simultaneously releasing functionality, which can facilitate introduction 2nd diversity. This not only provides set syntheses DNA‐conjugated drug‐like such ortho ‐alkenyl/sulfiliminyl/cyclopropyl phenol, benzofuran, dihydrobenzofuran but also paradigm for method development.

Language: Английский

Citations

9
Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(iii)-catalyzed cascade C–H functionalization/[3 + 2] dipolar cycloaddition DOI

Fu‐Xiaomin Liu,

Weijie Chen, Ying Cai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2512 - 2517

Published: Jan. 1, 2024

A Rh( iii )-catalysed cascade C–H functionalization/[3 + 2] dipolar cycloaddition was realized to deliver gem -difluorinated pentacyclic indenopyrazolopyrazolones with four continuous chiral carbon centres in a one-pot fashion.

Language: Английский

Citations

3
Rh(iii)-catalyzed redox-neutral C–H [4 + 1] annulation of sulfoximines with α,α-difluoromethylene alkynes: diastereoselective synthesis of E-monofluoroalkenyl benzoisothiazole 1-oxides DOI
Ting Wang,

Zhi‐Huan Peng,

Liexin Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5916 - 5922

Published: Jan. 1, 2023

Rh( iii )-catalyzed redox-neutral C–H [4 + 1] annulation of sulfoximines with α,α-difluoromethylene alkynes has been realized to diastereoselectively build E -monofluoroalkenyl benzoisothiazole 1-oxides.

Language: Английский

Citations

7
Cobalt-Catalyzed (3 + 2) Cycloaddition of Cyclopropene-Tethered Alkynes: Versatile Access to Bicyclic Cyclopentadienyl Systems and Their CpM Complexes DOI Creative Commons
Carlos Lázaro‐Milla, Eduardo da Concepción, Israel Fernández

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11574 - 11583

Published: July 20, 2024

Low-valent cobalt complexes can promote intramolecular (3 + 2) cycloadditions of alkyne-tethered cyclopropenes to provide bicyclic systems containing highly substituted cyclopentadienyl moieties with electronically diverse functional groups. The adducts be easily transformed into new types CpRh(III) and CpIr(III) complexes, which show catalytic activity in several relevant transformations. Preliminary computational (DFT) experimental studies information on the mechanistic peculiarities cobalt-catalyzed process allow us rationalize its advantages over homologous rhodium-promoted reaction.

Language: Английский

Citations

2
Enolate–Azide [3 + 2]-Cycloaddition Reaction Suitable for DNA-Encoded Library Synthesis DOI

Kangyin Pan,

Ying Yao, Yiyuan Zhang

et al.

Bioconjugate Chemistry, Journal Year: 2023, Volume and Issue: 34(8), P. 1459 - 1466

Published: July 14, 2023

The DNA-encoded chemical library (DEL) is a powerful hit selection technique in either basic science or innovative drug discovery. With the aim to circumvent issue concerning DNA barcode damage conventional on-DNA copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC), we have successfully developed first DNA-compatible enolate–azide [3 + 2] reaction. merits of this DEL chemistry include metal-free and high fidelity, conversions easy operation, broad substrate scope, ready access highly substituted 1,4,5-trisubstituted triazoles. Thus, it will not only further enrich toolbox but also great potential practical synthesis.

Language: Английский

Citations

6