Diastereoselective Access to Ester-Substituted cis-Phenanthridinones via Hydrogen Atom Transfer-Involved 1,7-Enyne Bicyclization DOI
Chuan Liu,

Zonglang Wu,

Guangpeng Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16632 - 16644

Published: Oct. 30, 2024

An organophotoredox-catalyzed 1,7-enyne bicyclization for the cis-diastereoselective synthesis of ester-substituted phenanthridinones has been achieved through radical cascade cyclization involving 1,6-hydrogen atom transfer. This transition-metal- and oxidant-free one-pot protocol generates three distinct C-C bonds two quaternary carbon centers.

Language: Английский

Oxo-Sulfonylation of 1,7-Enynes via a Multicomponent Oxidative Radical Polar Crossover Approach DOI
Pooja Yadav,

P. Sinha,

Purushothaman Gopinath

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

Diastereoselective synthesis of trans-3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein vinyl carbocation intermediate undergoes nucleophilic substitution to afford corresponding keto functional group. Deprotection N-Ts group, gram-scale synthesis, other synthetic applications were illustrated. Control experiments mechanistic studies show that water acts as nucleophile in this reaction.

Language: Английский

Citations

1
Recent Advances in the Cascade Cyclization Reactions of 1,7‐Enynes DOI

Xue‐Song Zhang,

Yaping Han, Yong‐Min Liang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 324 - 356

Published: Dec. 14, 2023

Abstract Elaborated molecular architectures, especially carbocyclic, heterocyclic, endocyclic, and polycyclic structures, serve as an important class of organic complexes because they are frequently occurring core structural units in a variety biologically pharmacologically relevant natural products, drug molecules, agrochemicals, functional materials. A main challenge current synthetic approaches is the development strategically efficient selective formation these compounds from easy‐to‐handle starting The cascade cyclizations 1,7‐enynes have afforded indispensable method for accessing complexity diversity, thus highlighting their potential significance both academic industrial communities. In last decades, tremendous efforts been devoted to discovering convenient routes access sophisticated annulation derivatives, wide range powerful straightforward strategies reported. this review, latest achievements cyclization reactions summarized, which could be separated into three categories: (1) Visible‐light‐induced 1,7‐enynes; (2) Metal‐free catalyzed (3) Transition‐metal‐catalyzed 1,7‐enynes.

Language: Английский

Citations

12
Demethylenative cyclization of 1,7-enynes using α-amino radicals as a traceless initiator enabled by Cu(i)-photosensitizers DOI

Qinfang Jiang,

Hanyang Bao,

Yun Peng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(50), P. 6399 - 6402

Published: Jan. 1, 2024

A rare type of demethylenative intramolecular cyclization 1,7-enynes to access quinoline-2-(1

Language: Английский

Citations

5
Advances in catalysis using Xantphos-like ligands; simplicity goes a long way DOI
Piet W. N. M. van Leeuwen, Israel Cano, Zoraida Freixa

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 537, P. 216636 - 216636

Published: April 11, 2025

Language: Английский

Citations

0
Diastereoselective Access to Ester-Substituted cis-Phenanthridinones via Hydrogen Atom Transfer-Involved 1,7-Enyne Bicyclization DOI
Chuan Liu,

Zonglang Wu,

Guangpeng Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16632 - 16644

Published: Oct. 30, 2024

An organophotoredox-catalyzed 1,7-enyne bicyclization for the cis-diastereoselective synthesis of ester-substituted phenanthridinones has been achieved through radical cascade cyclization involving 1,6-hydrogen atom transfer. This transition-metal- and oxidant-free one-pot protocol generates three distinct C-C bonds two quaternary carbon centers.

Language: Английский

Citations

1