ISHC2015

Diazocompounds are a very interesting class of compounds that can promote a wide range of reactions, such as cyclopropanations, insertion reactions, ylide formation, dimerization and elimination reactions and formation of ketenes by the Wolff rearrangement, among others. An interesting class of these diazocompounds is the α,β-unsaturated diazoketones, which has received little attention when compared to the saturated ones due to the difficulty of its preparation by the usual existing methods. Herein, we would like to describe two methodologies for the preparation of α,β-unsaturated diazoketones with E and Z geometry employing new Horner-Wadsworth-Emmons reagents and their use as efficient platforms in the synthesis of pyrrolidines, indolizidines and piperidines.