Regio- and Diastereoselective Cyclization Reactions of Free and Masked 1,3-Dicarbonyl Dianions with 1,2-Dielectrophiles

Abstract

Despite their simplicity and synthetic usefulness, cyclisation reactions of 1,3-dicarbonyl dianions with 1,2-dielectrophiles are problematic, since both dianions and 1,2-dielectrophiles are highly reactive compounds (low reactivity matching). In addition, 1,2-dielectrophiles are often rather labile, and reactions with nucleophiles can result in polymerisation, decomposition, formation of open-chained products, elimination or SET-reactions. These intrinsic limitations can be overcome by a proper reactivity tuning and by the use of electroneutral dianion equivalents (masked dianions) in Lewis acid catalysed reactions. The cyclisations reported herein allow for an efficient, regio- and stereoselective one-pot synthesis of biologically relevant ring systems.

Microwave irradiation: a green approach for the synthesis of functionalizedN-methyl-1,4-dihydropyridines

“… 20 Therefore, the preparation of 1,4-dihydropyridines is one of the most attractive areas of research for synthetic and medicinal chemists due to their diverse applications. For the synthesis of 1,4-DHPs, starting from the classical Hantzsch reaction, 21 a number of protocols have been reported. 22 …”