Diastereoselective Ring Expansion of Cyclic Ketones Enabled by HAT-Initiated Radical Cascade DOI
Wenxue Wang,

Shouyang Feng,

Yansheng Wei

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(44), P. 8022 - 8026

Published: Oct. 27, 2023

Herein we disclose an iron-catalyzed method for stereoselective synthesis of multisubstituted cyclic ketones containing a synthetically challenging quaternary carbon from readily accessible β-vinyl keto esters in good yields. This cascade reaction is initiated by hydrogen atom transfer (HAT) process, after which Dowd–Beckwith-type ring-expansion occurs. strategic transformation offers access to valuable bearing two contiguous stereocenters, including hold paramount significance within the realm synthetic chemistry.

Language: Английский

Photoinduced radical-polar crossover cyclization reactions DOI
Zhiming Zhu, Yongxin Zhang, Ziyang Li

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(5), P. 100945 - 100945

Published: March 5, 2024

Language: Английский

Citations

14
Toward the Generation of 2-Amino-3-Formyl Difunctionalized Chromones via Pd-Enabled Rearrangement Strategy DOI

Qi Tong,

Ren-Feng Xiu,

Jiahe Chen

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(19), P. 12692 - 12699

Published: Sept. 14, 2023

Accomplished herein is a rearrangement strategy for the highly efficient assembly of synthetically cumbersome while medicinally significant 2-amino-3-formyl chromones via palladium-catalyzed ring-opening, rearrangement, and cyclization process. Such sequence enables formation one C(sp2)–O bond C(sp2)–C(sp2) bond, reconstruction benzo-γ-pyrone moiety in single operation, thus producing difunctionalized chromone-incorporated derivatives. The reaction proceeds shorter time (30 min 3-iodochromones most cases) atom- step-economical manner. synthetic application current protocol further demonstrated by late-stage modification pharmaceuticals their intermediates, gram-scale reactions, transformations functional groups, as well synthesis bioactive molecules drugs. Mechanistic studies indicate that nucleophilic ring-opening process moiety, phenoxy anion intermediate, an intramolecular might be involved present system.

Language: Английский

Citations

21
Arylamine synthesis enabled by a photocatalytic skeletal-editing dehydrogenative aromatization strategy DOI Creative Commons

Yu-Feng Ren,

Xiaoyi Chen,

Hai‐Wu Du

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: 4(1), P. 100873 - 100873

Published: Jan. 1, 2024

Language: Английский

Citations

6
Cascade ring expansion reactions for the synthesis of medium-sized rings and macrocycles DOI Creative Commons
Jack M. Wootton, Jerry K. F. Tam, William P. Unsworth

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(38), P. 4999 - 5009

Published: Jan. 1, 2024

This Feature Article discusses recent advances in the development of cascade ring expansion reactions for synthesis medium-sized rings and macrocycles. Cascade have much potential use biologically important macrocycles, most notably as they don't require high dilution conditions, which are commonly used established end-to-end macrocyclisation methods. Operation by method can allow large products to be accessed

Language: Английский

Citations

5
Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer DOI Creative Commons
Jack M. Wootton,

Natalie J. Roper,

C. Morris

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A stereoselective strategy to make C–N atropisomeric amides based on intramolecular acyl transfer via a tethered Lewis basic pyridine or tertiary amine group is reported.

Language: Английский

Citations

0
Photoinduced radical alkylation of aldehydes with potassium alkyltrifluoroborates DOI

Kirill A. Zhilyaev,

Mikhail O. Zubkov, Mikhail D. Kosobokov

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3988 - 3996

Published: Jan. 1, 2024

A method for radical addition at aldehydes is described. The reaction based on the interplay of attack and cleavage processes occurring a boron complexed carbonyl group.

Language: Английский

Citations

2
Non-directed Oxidative Annulation of 2-Arylindazoles with Electron Deficient Olefins via Visible Light Photocatalysis DOI

Krishna Kanta Das,

Alakananda Hajra

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10402 - 10405

Published: Jan. 1, 2024

A new visible-light-mediated non-directed oxidative annulation between 2-arylindazoles and electron-deficient olefins using commercially available piperidine-1-sulfonyl chloride as the radical precursor to afford fused 5,6-dihydroindazolo[2,3-

Language: Английский

Citations

1
Diastereoselective Ring Expansion of Cyclic Ketones Enabled by HAT-Initiated Radical Cascade DOI
Wenxue Wang,

Shouyang Feng,

Yansheng Wei

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(44), P. 8022 - 8026

Published: Oct. 27, 2023

Herein we disclose an iron-catalyzed method for stereoselective synthesis of multisubstituted cyclic ketones containing a synthetically challenging quaternary carbon from readily accessible β-vinyl keto esters in good yields. This cascade reaction is initiated by hydrogen atom transfer (HAT) process, after which Dowd–Beckwith-type ring-expansion occurs. strategic transformation offers access to valuable bearing two contiguous stereocenters, including hold paramount significance within the realm synthetic chemistry.

Language: Английский

Citations

1