Conjugate systems in the construction of heterocycles and quaternary stereocenters

Abstract

The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good stereoisomeric ratios. The novel approach for the synthesis of benzofurans and indoles by intramolecular cyclization of enaminones has been applied in the preparation of furobenzofurans starting from benzo-bis-enaminones.