New frontiers of the Morita-Baylis-Hillman reaction: 1) New applications of a bifunctional catalyst derived from imidazole. 2) Studies on the asymmetric synthesis of a natural high-potency sweetener

Abstract

This PhD project aims to explore the potentiality of the Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of commercially important biologically active substances. The project is divided in two subprojects. In the first one, we intend to increase the scope for the use of a bifunctional base, recently used in our research group, as catalyst for the Morita-Baylis-Hilman reaction. We are interested in using unsaturated lactams, lactones and cyclic ketones for these reactions. We also intend to study the development of an asymmetric version for this reaction. In the second subproject, we will revisit the synthesis of a molecule from natural source, which presents a high activity as sweetener. A new proposal for the synthesis of Monatin will be the target of this subproject. We intend to use a Morita-Baylis-Hillman adduct as substrate for this asymmetric total synthesis. (AU)