Cited by Nitrogen-to-functionalized carbon atom transmutation of pyridine

Single-atom logic for heterocycle editing DOI

Justin Jurczyk, Jisoo Woo, Sojung F. Kim

et al.

Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(5), P. 352 - 364

Published: April 11, 2022

Language: Английский

Citations

280

Late-stage diversification of indole skeletons through nitrogen atom insertion DOI

Julia C. Reisenbauer, Ori Green, Allegra Franchino

et al.

Science, Journal Year: 2022, Volume and Issue: 377(6610), P. 1104 - 1109

Published: Sept. 1, 2022

Compared with peripheral late-stage transformations mainly focusing on carbon-hydrogen functionalizations, reliable strategies to directly edit the core skeleton of pharmaceutical lead compounds still remain scarce despite recent flurry activity in this area. Herein, we report skeletal editing indoles through nitrogen atom insertion, accessing corresponding quinazoline or quinoxaline bioisosteres by trapping an electrophilic nitrene species generated from ammonium carbamate and hypervalent iodine. This reactivity relies strategic use a silyl group as labile protecting that can facilitate subsequent product release. The utility highly functional group-compatible methodology context several commercial drugs is demonstrated.

Language: Английский

Citations

201

Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines DOI

Chunngai Hui,

Lukas Brieger, Carsten Strohmann

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(45), P. 18864 - 18870

Published: Nov. 8, 2021

Here we report a contractive synthesis of multisubstituted cyclobutanes containing multiple stereocenters from readily accessible pyrrolidines using iodonitrene chemistry. Mediated by nitrogen extrusion process, the stereospecific involves radical pathway. Unprecedented unsymmetrical spirocyclobutanes were prepared successfully, and concise, formal cytotoxic natural product piperarborenine B is reported.

Language: Английский

Citations

116

Skeletal Editing Approach to Bridge-Functionalized Bicyclo[1.1.1]pentanes from Azabicyclo[2.1.1]hexanes DOI

Brandon A. Wright, Anastassia Matviitsuk, Michael J. Black

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(20), P. 10960 - 10966

Published: May 5, 2023

Azabicyclo[2.1.1]hexanes (aza-BCHs) and bicyclo[1.1.1]pentanes (BCPs) have emerged as attractive classes of sp3-rich cores for replacing flat, aromatic groups with metabolically resistant, three-dimensional frameworks in drug scaffolds. Strategies to directly convert, or "scaffold hop", between these bioisosteric subclasses through single-atom skeletal editing would enable efficient interpolation within this valuable chemical space. Herein, we describe a strategy hop" aza-BCH BCP nitrogen-deleting edit. Photochemical [2+2] cycloadditions, used prepare multifunctionalized frameworks, are coupled subsequent deamination step afford bridge-functionalized BCPs, which few synthetic solutions currently exist. The modular sequence provides access various privileged bridged bicycles pharmaceutical relevance.

Language: Английский

Citations

Enantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing DOI

Jinteng Che,

Wei‐Yi Ding, Hongbo Zhang

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Language: Английский

Citations

Direct Deamination of Primary Amines via Isodiazene Intermediates DOI

Kathleen J. Berger, Julia L. Driscoll, Mingbin Yuan

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(42), P. 17366 - 17373

Published: Oct. 12, 2021

We report here a reaction that selectively deaminates primary amines and anilines under mild conditions with remarkable functional group tolerance including range of pharmaceutical compounds, amino acids, sugars, natural products. An anomeric amide reagent is uniquely capable facilitating the through intermediacy an unprecedented monosubstituted isodiazene intermediate. In addition to dramatically simplifying deamination compared existing protocols, our approach enables strategic applications iminium amine-directed chemistries as traceless methods. Mechanistic computational studies support intermedicacy which exhibits unexpected divergence from previously studied secondary isodiazenes, leading cage-escaping, free radical species engage in chain, hydrogen-atom transfer process involving aliphatic diazenyl intermediates.

Language: Английский

Citations

Molecular editing in natural product synthesis DOI

Chunngai Hui,

Zhuo Wang, Shiping Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(5), P. 1451 - 1457

Published: Jan. 1, 2022

Molecular editing entailing insertion and deletion of atom(s) enables new synthetic design the efficiency natural product synthesis could be improved.

Language: Английский

Citations

Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene DOI

Yao Zhou,

F Chen,

Ziru Li

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 1975 - 1981

Published: May 11, 2023

Language: Английский

Citations

Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes DOI

Keri A. Steiniger,

Matthew C. Lamb,

Tristan H. Lambert

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(21), P. 11524 - 11529

Published: May 18, 2023

A method for C(sp

Language: Английский

Citations

C(sp3)–C(sp3) bond formation through nitrogen deletion of secondary amines using O-diphenylphosphinylhydroxylamine DOI

Ting Guo, Jinghao Li,

Zhangkai Cui

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(7), P. 913 - 921

Published: June 7, 2024

Language: Английский

Citations