Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis

Abstract

An efficient oxidative NHC-catalyzed one-step transformation of (<i>S</i>)- or (<i>R</i>)-8-oxocitronellal to nepetalactone (NL) in enantio- and diastereomerically pure form has been developed. Several new and "easy to make" N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.