Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered <i>N</i>-Tosylhydrazones: Synthesis of Fused-Cyclopropane γ-Lactones

Abstract

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report the light-driven intramolecular cyclopropanation of alkene-tethered N -tosylhydrazones in the presence of Cs 2 CO 3 and visible light. We have synthesized various electronically and sterically substituted and heterocyclic-containing fused-(spiro)cyclopropane γ-lactone compounds in good yields under transition metal-free conditions using a radical-free approach. In addition, the one-pot synthesis of fused-cyclopropane γ-lactones from α-ketoesters and their synthetic utility are also presented.

Topics & Concepts