Cloke–Wilson rearrangement: a unique gateway to access five-membered heterocycles

Abstract

Cyclopropanes are of great synthetic value in heterocyclic chemistry due to their highly reactive nature. They are widely employed to synthesize various biologically active organic compounds. Generally, vinyl, carbonyl, imine, and alkylidene cyclopropanes are utilized as efficient synthetic precursors in organic synthesis. The Cloke–Wilson rearrangement of these activated cyclopropanes is carried out to achieve the synthesis of diverse heterocyclic scaffolds. Various oxygen, nitrogen, and sulfur-containing heterocyclic compounds have been synthesized employing this rearrangement. With time, Cloke–Wilson rearrangement has evolved into a high yielding enantioselective and diastereoselective approach utilizing integrated novel methods. Our review focuses on the recent approaches for Cloke–Wilson rearrangement to synthesize several five-membered heterocycles and its applicability towards the natural product syntheses reported during 2000–2020.