Electrophilic Halospirocyclization of N-Benzylacrylamides to Access 4-Halomethyl-2-azaspiro[4.5]decanes

An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize a wide variety of 4-halomethyl-2-azaspiro[4.5]decanes with satisfactory yields. The approach is further highlighted through gram-scale synthesis and diverse transformations of the spiro products.

Automated summary

An electrophilic spirocyclization reaction using N-halosuccinimides as halogenating reagents has been developed. This reaction provides a fast and efficient method to synthesize various 4-halomethyl-2-azaspiro[4.5]decanes without the need for metal reagents, photochemistry, or electrochemistry.