9H-Cyclohepta­[b]­pyridin-9-one was used as a diene cycloaddition partner to construct [3.2.2] bicycles in a copper-catalyzed [4+2] cycloaddition. Oxygen- and nitrogen-substituted terminal, disubstituted, trisubstituted, and cyclic alkenes reacted to afford the cycloadducts as single constitutional isomers in 48–80% yields and diastereomeric ratios up to 5.6:1.

Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination-nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

A general protocol for the enantioselective synthesis of 3‐heterosubstituted‐2‐amino‐1‐ols was developed based on metal‐ free intramolecular regio‐ and stereoselective diene aziridination and regioselective opening. Kinetic resolution of the resulting (1′‐NR1R2 and 1′‐SR)‐4‐oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.

No abstract