Inverting the Regioselectivity of 1,3-Dipolar Cycloaddition Reaction Between Nitrones and Enal Derivatives

Key Points

• The study aims to explore the inversion of regioselectivity in the reaction of nitrones with enal derivatives.
• Analyzed the cycloaddition reactions between nitrones and enal derivatives.
• Utilized frontier orbital theory to explain observed regioselectivity outcomes.
• Produced 5-iminoisoxazolidines and 4-acylisoxazolidines as major products.
• The reaction between nitrones and hydrazones primarily yields 5-iminoisoxazolidines.
• Conversely, enal reactions consistently yield 4-acylisoxazolidines.
• A shift in regioselectivity is attributed to the theoretical framework of frontier orbital interactions.