An Efficient Lewis Acid Catalyzed Povarov Reaction for the One-Pot Stereocontrolled Synthesis of Polyfunctionalized Tetrahydroquinolines

An easy and efficient synthetic methodology for the one-pot stereocontrolled synthesis of tetrahydroquinolines through Lewis acid activated Povarov reaction is described. The protocol takes advantage of the very cheap, easy to handle, and environmentally friendly cerium trichloride as catalyst and allows to obtain either the anti- or the syn-isomer of the final tetrahydroquinoline with good selectivity, by performing the reaction in solvent or solventless conditions. The scope of the reaction is expanded to the one-pot synthesis of N-alkyltetrahydroquinolines through a very efficient iminium-Povarov approach. A deeper insight on the reaction system was provided by the study on the side reactions occurring in the reaction conditions and on the nature of the stereoselectivity

Influence of metallic cations in the witting reaction: useful step for the synthesis of anticancer agents

Alkenes with a well defined geometric configuration represent an essential class of key intermediates, and they are a continuous challenge in the synthesis of many natural products and drugs. Different methodologies have been developed, and the Wittig reaction and related transformations for its high level of geometrical control have become the most frequently employed. The counter ion of the base used can be choose in order to obtain different stereoselectivity in Wittig reactions, and in recent years, our efforts are focused on the study of the presence of cerium for a better selectivity towards the formation of (Z)-alkenes. In nature (Z)-alkenes are abundant and capital importance for their biological activity, for this we interested at the synthesis of hydroxyl-substituted alkenylbenzenes because they are effective anticancer agents. Typical component of this family is the (Z)-Climacostol, a toxin belonging to the family of resorcinolic lipids. It is present in prokaryotes as well as in single-celled and multicellular eukaryotes and has attracted great attention due its antimicrobial, cytotoxic and anticancer activities

Catalyst-Free Synthesis of Polysubstituted 5-Acylamino-1,3-Thiazoles via Hantzsch Cyclization of α-Chloroglycinates

A catalyst-free heterocyclization reaction of α-chloroglycinates with thiobenzamides or thioureas leading to 2,4-disubstituted-5-acylamino-1,3-thiazoles has been developed. The methodology provides straightforward access to valuable building blocks for pharmaceutically relevant compounds.Science, Faculty ofNon UBCChemistry, Department ofReviewedFacult