Construction of nine-membered N,N,O-heterocycles via Pd-catalyzed [6+3] dipolar cycloaddition

A new approach for the synthesis of 9-membered N,N,O-heterocycles by Pd-catalyzed [6+3] dipolar cycloaddition of N-iminoisoquinolinium ylides and 2-vinyl oxetanes has been developed. The scope of this cycloaddition was demonstrated with 28 examples. This is another important synthetic strategy for medium-sized rings by employing N-iminoisoquinolinium ylides as ternary synthons.

Automated summary

This article describes a new synthetic approach for the synthesis of 9-membered N,N,O-heterocycles using Pd-catalyzed [6+3] dipolar cycloaddition. The scope of this cycloaddition is demonstrated with 28 examples, highlighting the importance of using N-iminoisoquinolinium ylides as ternary synthons for medium-sized ring synthesis.