Arnaud Martel

Responsabilities

-          Head of the MSO research team since January 2016

-          In charge of the « licence professionnelle Industries chimiques et pharmaceutiques, Analyse chimique et contrôle des matériaux » since 01/09/2014.

-                  Head of the chemistry department of IUT du Mans from 01/05/2010 to 01/09/2013

-          Member of the research unit council since 2012

EduCation, Work experience and scientific production

Since Sep 2013 : Professor, IUT Le Mans

Sep 2004-Sep 2013    Associate Professor, IUT du Mans.

Dec 2010        Habilitation to research supervision, Université du Maine, Le Mans.

Apr 2003-Sep 2004    UppsalaUniversity (Sweden), Post-Doctoral position, Henrik Ottosson team. Marie Curie fellowship.

Mars 2002-Mars 2003           ICOA, Orléans University, Industrial Post-doctoral position, Gerald Guillaumet.

Sep 2001         PhD Organic Chemistry, Université du Maine, Le Mans.

 

Resarch interest and participation to research projects

-          Methodology in Organic Chemistry: Heterocycloadditions [3+2] and [4+2]

-          DFT elucidation of reaction pathways.

-          Participation to research projects: ANR JCJC RECYTIN, ANR OXAPROL, ANR KIDAMYSYN, Region Pays de Loire network projects: CIMATH, PIRAMID.

 

Publications

  • Enantioselective Access to Robinson Annulation Products and Michael Adducts as Precursors (Arnaud Martel - Gallier - Florian; Martel - Arnaud ; Dujardin - Gilles, 2017)

    The Robinson annulation is a reaction that has been useful for numerous syntheses since its discovery in 1935, especially in the field of steroid synthesis. The products are usually obtained after three consecutive steps: the formation of an enolate (or derivative), a conjugate addition, and an aldol reaction. Over the years, several methodological improvements have been made for each individual step or alternative routes have been devised to access the Robinson annulation products. The first part of this Review outlines the most relevant developments towards the formation of monocarbonyl-derived Robinson annulation products (MRA products, MRAPs) and activated monocarbonyl-derived Robinson annulation products (AMRA products, AMRAPs). The following sections are then devoted to the diastereoselective and enantioselective synthesis of these products, while the last section describes the enantiomeric resolution of racemic mixtures.

    See the online publication

  • Chemo-, Regio-, and Stereoselective Synthesis of Polysusbtituted Oxazolo[3,2-d][1,4]oxazepin-5(3H)ones via a Domino oxa-Michael/aza-Michael/Williamson Cycloetherification Sequence (Arnaud Martel - El Bouakher Abderrahman - Tasserie Jordan - Le Goff Ronan - Lhoste Jérôme - Martel Arnaud - Comesse Sébastien, 2017)

    The access to new oxazolo[3,2-d][1,4]oxazepin-5(3H)-ones starting from α-bromoamido alcohols and Michael acceptors under mild conditions is presented. This domino process proved to be chemo-, regio-, and stereoselective and allows the formation of a large diversity of highly functional 7-membered rings in good yields up to 95%. The complete shift of the regioselectivity of the intermediate enolate from a C–C to a C–O bond formation, contrary to the already known alkylations of such ambident nucleophiles, is mostly triggered by steric effects. The last step of the sequence was modeled by DFT giving some important insights for this C–C vs C–O bond shift.

    See the online publication

  • Oxa–diketopiperazines: Access and Conformational Analysis of Potential Turn Inducers (Arnaud Martel - Berthet Mathéo - Lebrun Aurélien - Martel Arnaud - Cheviet Thomas - Martinez Jean - Parrot Isabelle, 2017)

    An improvement of the 1,2,5-oxadiazine-3,6-diones (Oxd) synthesis and reactivity is described in this paper. The methodology has been successfully applied to produce a library of this poorly studied scaffold, which can be considered as an oxa-diketopiperazine (oxa-DKP). Significantly, the first crystal structures of oxa-DKP were obtained and compared to the diketopiperazine ring. Finally, a straightforward procedure concerning the coupling of various amino acids with oxa-DKP heterocycles to afford original peptidomimetics was reported. The conformational analysis realized on di- and tripeptide analogs revealed that the oxa-DKP skeleton exhibited remarkable β-turn inducer properties.

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  • Enantioselective 1,3-Dipolar Cycloaddition Reactions of C-Carboxy Ketonitrones and Enals with MacMillan Catalysts: Evidence of a Nonconcerted Mechanism (Arnaud Martel - Ben Ayed Kawther - Laurent Mathieu Y. - Martel Arnaud - Selim Khalid - B. Abid Souhir - Dujardin Gilles, 2017)

    Highly diastereo- and enantioselective 1,3-dipolar cycloadditions between functional ketonitrones and β-substituted enals are promoted by MacMillan imidazolidinium organocatalysts. A study of the reaction scope shows that high selectivities are conserved if the N-protecting group or the ester function is varied. However, the reaction is sensitive to steric interactions with the C substituent of the nitrone. In all cases, the reaction proceeds with high exo selectivity. In most cases, a third diastereomer, incompatible with a concerted mechanism, was also observed, albeit in minute amounts. DFT calculations suggest that the cycloaddition proceeds in a nonconcerted fashion by an initial oxa-Michael-type addition of the nitrone to the double bond followed by a cyclization. This mechanism explains the formation of the observed minor diastereomers. In addition, the diastereo- and enantioselectivities of the reaction were shown to be intermediately thermodynamically controlled, and the diastereomeric ratio is modulated by the kinetics of iminium hydrolysis.

    See the online publication