Expeditious synthesis of N-bridged heterocycles via dipolar cycloaddition of pentafulvenes with 3-oxidopyridinium betaines

Abstract

A new and highly versatile approach towards the synthesis of bicyclo[6.3.0]undecanes and bicyclo[5.3.0]decanes was accomplished. The methodology adopted involved [6+3] and [3+2] cycloaddition reactions of pentafulvenes with 3-oxidopyridinium betaines generated either by the action of a base on the pyridinium salt or thermally from pyridinium betaine dimer. These well-functionalized bicyclo[6.3.0]undecanes and bicyclo[5.3.0]decanes offer a wide range of synthetic options, which can be expected to translate into a variety of rapid and efficient synthesis of natural products.