Synthesis of Polysubstituted 2-Piperidinones via a Michael Addition/ Nitro-Mannich/Lactamization Cascade.

An efficient and practical method has been developed for the diversity-oriented synthesis of polysubstituted 2-piperidinones via four-component reaction between substituted nitrostyrenes, aromatic aldehydes, ammonium acetate, and dialkyl malonates for the generation of a wide range of structurally interesting and pharmacologically significant compounds. It is worth mentioning that in the course of this reaction, the formation of products was highly stereoselective. Two differently stereochemical classes of polysubstituted 2-piperidinones depended on the substitutent position of aromatic aldehyde. [ABSTRACT FROM AUTHOR]