Merging Nucleophilic Phosphine Catalysis and Photocatalysis for the Rapid Assembly of 2-Oxabicyclo-[2.1.1]hexane Scaffolds from Feedstock Allyl Alcohols DOI Creative Commons
David M. Whalley, Luca Carlino, Okky Dwichandra Putra

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The previously unreported combination of nucleophilic phosphine catalysis and energy transfer allows for the rapid construction structurally distinct 2-oxabicyclo[2.1.1]hexanes (2-oxa-BCH) from readily available building blocks with high atom economy. Previous multistep routes to these important phenyl ring bioisosteres have largely depended on use bespoke strain-release agents or multiple post-functionalisation reactions access structural diversity scaffold. In contrast, this cascade reaction medicinal chemist exploit breadth commercial allyl alcohols synthesise systematically diverse 2-oxa-BCH architectures. Using a polar radical disconnections in same flask, every position scaffold can be substituted useful functional handles such as protected amines, esters alcohols, well arenes alkyl groups. Cyclic even employed yield single diastereomers sp

Language: Английский

Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones DOI

Lan Zheng,

Yumin Yang, Zhiping Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed. The reaction enables the construction spirobicyclo[2.1.1]hexanes bearing an all-carbon quaternary center in moderate to good yields excellent diastereoselectivities. This method features a broad substrate scope functional group compatibility. practical utility this protocol was further demonstrated by gram-scale synthesis and postsynthetic transformations desired product.

Language: Английский

Citations

3

Synthetic Strategies and Applications of Fluorine‐Containing Bridged Bicyclic Compounds DOI Creative Commons
Simone Baldon, Luca Dell’Amico, Sara Cuadros

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(43)

Published: Aug. 5, 2024

Abstract Bridged bicyclic compounds (BBCs) have recently emerged as effective 3D‐isosteres of planar aryl and heteroaryl rings. Current synthetic endeavours are devoted to accessing these complex structures bearing functionalities in different positions the aliphatic Of particular interest is incorporation F‐containing motifs, since it allows generation isosteric units with improved physicochemical properties, including lipophilicity, water solubility, or oxidative resistance.

Language: Английский

Citations

1

Access to 2-Oxabicyclo[2.1.1]hexanes and their use in Scaffold Hopping DOI
Olivier Lorthioir, Niall A. Anderson, Scott D. Boyd

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9179 - 9184

Published: Oct. 21, 2024

Saturated isosteres of the

Language: Английский

Citations

1

Merging Nucleophilic Phosphine Catalysis and Photocatalysis for the Rapid Assembly of 2-Oxabicyclo-[2.1.1]hexane Scaffolds from Feedstock Allyl Alcohols DOI Creative Commons
David M. Whalley, Luca Carlino, Okky Dwichandra Putra

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The previously unreported combination of nucleophilic phosphine catalysis and energy transfer allows for the rapid construction structurally distinct 2-oxabicyclo[2.1.1]hexanes (2-oxa-BCH) from readily available building blocks with high atom economy. Previous multistep routes to these important phenyl ring bioisosteres have largely depended on use bespoke strain-release agents or multiple post-functionalisation reactions access structural diversity scaffold. In contrast, this cascade reaction medicinal chemist exploit breadth commercial allyl alcohols synthesise systematically diverse 2-oxa-BCH architectures. Using a polar radical disconnections in same flask, every position scaffold can be substituted useful functional handles such as protected amines, esters alcohols, well arenes alkyl groups. Cyclic even employed yield single diastereomers sp

Language: Английский

Citations

0