Enantioselective Synthesis of 3-Heterosubstituted-2-amino-1-ols by Sequential Metal-Free Diene Aziridination/Kinetic Resolution.

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'-NR1 R2 and 1'-SR)-4-oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.

Copper-Catalyzed [4+2] Cycloaddition of 9 H-Cyclohepta[ b]pyridine-9-one and Electron-Rich Alkenes.

9 H-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.

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis.

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.