One-pot stereoselective synthesis of aza-heterocycles Sébastien Comesse, Alahyen, V. Dalla, C. Taillier Université du Havre, France
Our society is in demand of a more sustainable economic system more respectful of the environment. From a chemistry point of view, one way to assert this is by developing strategies generating less wastes while consuming less hazardous reagents and energy such as domino reactions, which imply the formation of two or more bonds in one-step under the same reaction conditions in a well-defined order. 1 Their potential is enhanced when these reactions are coupled with the use of organocatalytic processes with the capacity to selectively generate undiscovered molecules of high added value. Our team is interested in the improvement of synthetic pathways by exploring new catalytic reactions and one-pot approaches to access novel and complex molecular structures. Over the years, we have published several papers on the domino synthesis of polysubstituted γ- and δ-lactams employing simple substrates such as haloacetamides 2 and Michael acceptors. 3 Mechanistic understanding of the domino processes is essential to improve reactions, but even more crucially to alter the course of a process. Thus, by a simple change of the conditions, different products can be obtained from the same reactants. The main goal of the present project is the development of new catalytic domino pathways starting now from N -alkoxyacrylamides. 4 Thanks to the alkoxy moiety on the nitrogen atom, d-lactam could be isolated in good yields and stereoselectivity. 5 By tuning the reaction conditions, another family of attractive polysubstituted lactams bearing an exocyclic double bond was obtained by a new organocatalyzed domino aza-Michael/Morita- Baylis-Hillman sequence . An access to enantioenriched products starting from N -alkoxyacrylamides is currently underway in our Laboratory. References 1. L. F. Tietze, Chem. Rev. 1996 , 96 , 115-136; b) H. Pellissier, Chem. Rev. 2013 , 113 , 442-524. 2. A. Fantinati, V. Zanirato, P. Marchetti, C. Trapella, ChemistryOpen 2020 , 9 , 100-170; 3. A. El Bouakher, A. Martel, S. Comesse, Org. Biomol. Chem. 2019 , 17 , 8467-8485 a) S. Comesse, M. Sanselme, A. Daïch, J. Org. Chem. 2008 , 73 , 5566-5569; 4. I. Allous, S. Comesse, M. Sanselme, A. Daïch, Eur. J. Org. Chem. 2011 , 5303-5310; 5. M. Saber, S. Comesse, V. Dalla, A. Daïch, M. Sanselme, P. Netchitaïlo, Synlett. 2010 , 2197-2201. 6. I. Alahyen, L. Benhamou, V. Dalla, C. Taillier, S. Comesse, Synthesis 2021 , 53 , 3409-3439 7. P. Champetter, O. Castillo-Aguilera, C. Taillier, J.-F. Brière, V. Dalla, S. Oudeyer, S. Comesse , Eur. J. Org. Chem. 2019 , 7703-7710.
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