Highly chemo- and diastereo-selective synthesis of 2,6-diazabicyclo[3.2.0]heptan-7-ones, pyrrolidines and perhydroazirino[2,3-c]pyrroles

Abstract

The manuscript describes a simple, convenient and metal-free diastereoselective synthesis of 4-halo-3-aryl/alkyl-6-aryl-2,6-diazabicyclo[3.2.0]heptan-7-ones via intramolecular endo-trig haloamination of 3-aminoazetidin-2-ones and its facile transformations to previously unknown methyl 4-halo-3-arylaminopyrrolidine-2-carboxylates and N-deprotected diazabicyclo[3.1.0]-hexane-2-carboxylic acids in good yields. The synthesis of such heterocyclic system is important in terms of the usefulness as organic synthon as well as their diverse pharmacological profiles.