Photoredox-catalysed amidyl radical insertion to bicyclo[1.1.0]butanes DOI Creative Commons
Chetan C. Chintawar, Ranjini Laskar,

Debanjan Rana

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(11), P. 1232 - 1242

Published: Oct. 22, 2024

Abstract Replacing planar aromatic rings in drug molecules with C( sp 3 )-rich isosteric mimetics, such as bicyclo[ n .1.1]alkanes, can significantly alter their physicochemical and pharmacokinetic properties, often leading to higher clinical success rates. However, unlike a benzene ring, the structurally rigid mimetics of heteroaromatic are rare. Heterobicyclo[ .1.1]alkanes promising this regard, but lack modular synthetic methods has currently hindered exploration. We envisioned that strategic selective insertion different heteroatomic units bicyclo[1.1.0]butanes could offer highly platform access diverse heterobicyclo[ .1.1]alkanes. Herein we report photoredox-catalysed regioselective chemoselective amidyl radicals bicyclo[1.1.0]butanes, providing direct 2-oxa-4-azabicyclo[3.1.1]hept-3-enes. The exit vector analysis shows geometric resemblance these heterobicyclic motifs pyridine pyrimidine derivatives, suggesting potential medicinally important heterocycles. Additionally, various downstream transformations demonstrate utility versatile building blocks chemistry.

Language: Английский

Palladium-catalysed [2σ + 2π] cycloaddition reactions of bicyclo[1.1.0]butanes with aldehydes DOI

Tianzhu Qin,

Mengyang He,

Weiwei Zi

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

Language: Английский

Citations

15
Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes DOI Creative Commons
Avishek Guin,

Shiksha Deswal,

Mahesh Singh Harariya

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(31), P. 12473 - 12479

Published: Jan. 1, 2024

Bicyclo[1.1.0]butanes (BCBs), featuring two fused cyclopropane rings, have found widespread application in organic synthesis. Their versatile reactivity towards radicals, nucleophiles, cations, and carbenes makes them suitable for various reactions, including ring-opening annulation strategies. Despite this versatility, their potential as enophiles an ene reaction remains underexplored. Considering given the challenges of achieving diastereoselectivity reactions BCBs, herein, we present a unique method utilizing BCBs mild diastereoselective Sc(OTf)

Language: Английский

Citations

13
Photocatalytic Oxidative Activation of Bicyclo[1.1.0]butanes for Formal [2σ+2π] Cycloadditions DOI Creative Commons
Maxim Golfmann,

Marius Reinhold,

Jorn D. Steen

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 13987 - 13998

Published: Sept. 6, 2024

Language: Английский

Citations

13
Pyridine-boryl radical-catalyzed [3π + 2σ] cycloaddition for the synthesis of pyridine isosteres DOI
Yuan Liu,

Shuang Lin,

Zhengwei Ding

et al.

Chem, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 1, 2024

Language: Английский

Citations

12
Photoredox-catalysed amidyl radical insertion to bicyclo[1.1.0]butanes DOI Creative Commons
Chetan C. Chintawar, Ranjini Laskar,

Debanjan Rana

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(11), P. 1232 - 1242

Published: Oct. 22, 2024

Abstract Replacing planar aromatic rings in drug molecules with C( sp 3 )-rich isosteric mimetics, such as bicyclo[ n .1.1]alkanes, can significantly alter their physicochemical and pharmacokinetic properties, often leading to higher clinical success rates. However, unlike a benzene ring, the structurally rigid mimetics of heteroaromatic are rare. Heterobicyclo[ .1.1]alkanes promising this regard, but lack modular synthetic methods has currently hindered exploration. We envisioned that strategic selective insertion different heteroatomic units bicyclo[1.1.0]butanes could offer highly platform access diverse heterobicyclo[ .1.1]alkanes. Herein we report photoredox-catalysed regioselective chemoselective amidyl radicals bicyclo[1.1.0]butanes, providing direct 2-oxa-4-azabicyclo[3.1.1]hept-3-enes. The exit vector analysis shows geometric resemblance these heterobicyclic motifs pyridine pyrimidine derivatives, suggesting potential medicinally important heterocycles. Additionally, various downstream transformations demonstrate utility versatile building blocks chemistry.

Language: Английский

Citations

12