Skeletal Editing of Isoindolines to Tetralins
Bowei Huang1, Jiaqi Zou1, Saizhou Wang1
1State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Abstract:
We present a skeletal editing strategy for transforming isoindolines into tetralins via a cascade N-atom removal deconstruction followed by a Diels-Alder reaction between in situ generated o-quinodimethanes and activated alkenes. This approach features a broad substrate scope, excellent stereoselectivity, and high yields, demonstrating its applicability to complex bioactive compounds and natural products. Notably, case studies showcase the efficient construction of challenging spirocyclic and bridged systems, underscoring the method's versatility and potential for advancing applications in synthetic chemistry.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Stereoisomerism of Cyclic Compounds
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Structural Isomerism
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
