Dipolar 3+2 Cycloaddition of Nitrones to 3-Aroylpyrrolo2,1-c1,4benzothiazine-1,2,4-triones

Key Points

• The aim is to explore the dipolar [3+2]-cycloaddition of nitrones with specific benzothiazine derivatives to determine diastereomer formation.
• Conducted dipolar [3+2]-cycloaddition reactions with diarylnitrones and 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones.
• Analyzed the resulting products for stereoselectivity and diastereomer formation.
• Utilized density functional theory to model and predict reaction outcomes.
• Identified exclusive formation of (2aS*,3R*,5aS*) diastereomers from the cycloaddition.
• Demonstrated that the (2aS*,3R*,5aS*) diastereomers are both kinetically and thermodynamically preferred.
• Observed that cycloadducts can revert to starting materials, influenced by the nitrone substituent's electronic properties.