The MARDi cascade : A Michael-Initiated Domino-Multicomponent Approach for the Stereoselective Synthesis of Seven-Membered Rings

International audienceThe MARDi cascade is a recently invented three-component condensation involving 1,3-dicarbonyl derivatives. It allows the regio- and stereocontrolled access to a variety of functionalized and substituted seven-membered rings. The substitution array can be diastereoselectively modulated by appropriate choice of the reaction partners, and the reaction allows the control of up to five newly created stereocenters and a complete chiral induction in the case of an optically active ketone precursor. The high level of diastereoselectivity observed has been attributed to a total thermodynamical control of the reaction. The attractiveness of the present domino three-component approach to seven-membered rings resides in the diversity of carbo- and heterocyclic structures that can be accessed with total regiocontrol and high stereocontrol starting from simple substrates, under user and environmentally friendly conditions, as now required in modern organic chemistry