Bicyclic imides with bridgehead nitrogen. Synthesis of an anti-Bredt bicyclic hydantoin

Abstract

Here we described the first synthesis of an anti-Bredt bicyclic imide from the hydantoin class, structure 5 (n = 2). As was also observed for the 2,4-oxazolidinedione class bicyclo[4.2.1]nonane 5 appears to contain the smallest methylene bridge that allows for preparation, isolation, and handling under normal conditions