Institut de Chimie Moléculaire et des Matériaux d'Orsay

Laboratoire de Chimie des Procédés et des Substances Naturelles- LCPSN

Synthetic Methodologies

Cyrille Kouklovsky,Guillaume Vincent, Valérie Alezra, Annie Pouilhès, Pierre Sancibrao, Rodolphe Beaud

Methodological studies in our group are driven towards the preparation of chiral, nitrogen-containing small building blocks.  Our current work is focusing on the nitroso Diels-Alder reaction, the catalytic asymmetric hydroamination reaction, and the ring rearangement methathesis of nitroso Diels-Alder cycloadducts.

Nitroso Diels-Alder reaction: We are interested in the development of new nitroso Diels-Alder (including asymmetric Diels-Alder) reactions and their synthetic applications.  We have recently introduced  α-acetoxynitroso derivatives as new dienophiles for the nitroso Diels-alder reaction.  These compounds may react under two conditions : either in water without any catalyst, or in the presence of a Lewis acid in aprotic medium.  We are currently working on the asymmetric version of this reaction using chiral reagents or catalysts.

Catalytic asymmetric hydroamination: in a collaboration with the « Catalyse moléculaire » team in our Institute, we are studying the catalytic asymmetric intramolecular hydroamination reaction, with chiral lanthanide-based catalysts.  Our team is focusing on the synthetic potential of this reaction, especially in the field of alkaloid synthesis.

Ring Rearrangement Methathesis reactions: We have recently demonstrated that the ring rearrangement methathesis reaction could be performed on nitroso Diels-Alder cycloadducts, provided that a cross-methathesis partner is added to the reaction mixture. Scope and applications of this reaction are currently under investigation in our group.