Ruthenium Porphyrin Catalyzed Intramolecular Carbenoid C−H Insertion. Stereoselective Synthesis of Cis-Disubstituted Oxygen and Nitrogen Heterocycles

Abstract

A ruthenium porphyrin-catalyzed stereoselective intramolecular carbenoid C−H insertion is described. Using [RuII(TTP)(CO)] as catalyst, aryl tosylhydrazones are converted to 2,3-dihydrobenzofurans, 2,3-dihydroindoles, and β-lactams in good yields and remarkable cis selectivity (up to 99%). Enantioselective synthesis of 2,3-dihydrobenzofurans is also achieved with [RuII(D4-Por*)(CO)] as catalyst, and up to 96% ee is attained.