Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: Diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals

Abstract

In this paper we describe new multi-catalysis cascade (MCC) reactions for the one-pot synthesis of highly functionalized non-symmetrical malonates. These metal-free reactions are either five-step (olefination/hydrogenation/alkylation/ ketenization/esterification) or six-step (olefination/hydrogenation/alkylation/ ketenization/esterification/alkylation), and employ aldehydes/ketones, Meldrum's acid, 1,4-dihydropyridine/o-phenylenediamine, diazomethane, alcohols and active ethylene/acetylenes, and involve iminium-, self-, self-, self- and base-catalysis, respectively. Many of the products have direct application in agricultural and pharmaceutical chemistry. © 2009 The Royal Society of Chemistry.