Diazomethane-Mediated Synthesis of Azetidine-Embbedd Tetracyclic System

What is it about?

The first diazomethane-mediated synthesis of azetidine-embedded tetracyclic ketal systems is reported. Reactions of norbornyl hemiaminal acetals with diazomethane afford azetidine-embedded tetracyclic ketals in good to excellent yields. The bridgeheadbromo-substituted hemiaminal acetals give higher yields compared to the corresponding bridgehead-chloro-substituted hemiaminal acetals. The hemiaminal acetals are prepared stereoselectively via nucleophilic addition of various amines to norbornyl α-diketones from the exo face.

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Why is it important?

First diazomethane-mediated synthesis of the azetidine