- Adresse : 5 mail Gay-Lussac 95000 Neuville-sur-Oise
Access to C-glycosides by directed metal-catalyzed C-H functionalisation at the anomeric position:
The importance of carbohydrates in biology pushes to develop new accesses to build them efficiently and in particular their C-glycosides analogs. However, current synthetic routes to these structures involve several steps. Recently, access to complex molecules via C-H functionalisation became very attractive since it avoids having to go through prefunctionalized intermediates. To overcome regioselectivity issues, the use of directing groups is commonly chosen in metal-catalyzed C-H functionalisation (MCF). However, examples of MCF on sugars are very limited. In this project, we aim to develop new, general and efficient MCF methods to access to diverse C-aryl-glycosides of interest.
The importance of carbohydrates in biology pushes to develop new accesses to build them efficiently and in particular their C-glycosides analogs. However, current synthetic routes to these structures involve several steps. Recently, access to complex molecules via C-H functionalisation became very attractive since it avoids having to go through prefunctionalized intermediates. To overcome regioselectivity issues, the use of directing groups is commonly chosen in metal-catalyzed C-H functionalisation (MCF). However, examples of MCF on sugars are very limited. In this project, we aim to develop new, general and efficient MCF methods to access to diverse C-aryl-glycosides of interest.
Discipline(s) enseignée(s)
Organic Chemistry (practical and tutorial courses) at IUT Génie-Biologique
Activités / CV
PUBLICATIONS:
[1] Glycosamine derivatives through metal-catalyzed C-N bond formation on protected and unprotected 2-iodoglycals.
Malinowski, M.; Banoun, C.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Eur. J. Org. Chem. 2021, DOI:10.1002/ejoc.202001618
[2] Emerging Organometallic Methods for the Synthesis of C-Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches. Ghouilem, J.*; de Robichon, M.*; Le Bideau, F.; Ferry, A.; Messaoudi, S. Chem. Eur. J. 2021, 27, 491-511 * = contributed equally
[3] Mild Palladium-Catalyzed Cyanation of Unprotected 2-Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2-Glycoanalogues.
Malinowski, M.; Tran, T. V.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Adv. Synth. Catal. 2020, 362, 1184-1189
[4] Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates. de Robichon, M.; Bordessa, A.; Malinowski, M.; Uziel, J. ; Lubin-Germain, N.; Ferry, A. Chem. Commun. 2019, 55, 11806-11808
[5] “CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2-Iodoglycals. de Robichon, M.; Bordessa, A.; Lubin- Germain, N.; Ferry, A. J. Org. Chem. 2019, 84, 3328-3339
[1] Glycosamine derivatives through metal-catalyzed C-N bond formation on protected and unprotected 2-iodoglycals.
Malinowski, M.; Banoun, C.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Eur. J. Org. Chem. 2021, DOI:10.1002/ejoc.202001618
[2] Emerging Organometallic Methods for the Synthesis of C-Branched (Hetero)aryl, Alkenyl, and Alkyl Glycosides: C−H Functionalization and Dual Photoredox Approaches. Ghouilem, J.*; de Robichon, M.*; Le Bideau, F.; Ferry, A.; Messaoudi, S. Chem. Eur. J. 2021, 27, 491-511 * = contributed equally
[3] Mild Palladium-Catalyzed Cyanation of Unprotected 2-Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2-Glycoanalogues.
Malinowski, M.; Tran, T. V.; de Robichon, M.; Lubin-Germain, N.; Ferry, A. Adv. Synth. Catal. 2020, 362, 1184-1189
[4] Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates. de Robichon, M.; Bordessa, A.; Malinowski, M.; Uziel, J. ; Lubin-Germain, N.; Ferry, A. Chem. Commun. 2019, 55, 11806-11808
[5] “CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2-Iodoglycals. de Robichon, M.; Bordessa, A.; Lubin- Germain, N.; Ferry, A. J. Org. Chem. 2019, 84, 3328-3339
POSTERS:
*JCO at Polytechnic University, Palaiseau, France, October 29th to 31st, 2019 - Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates.
*RCO at ICSN, CNRS Paris-Saclay University, April 19th 2019 - “CO” as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki–Miyaura Reaction from 2- Iodoglycals. • ORAL COMMUNICATION:
*Day of PhD students in BioCIS Laboratory, virtual symposium, February 11th, 2021 - Access to C-glycosides by directed metal-catalyzed C-H functionalisation of the anomeric position.
AWARD:
“Women and Sciences” award 2021 of the CY Alliance (CY Cergy Paris University).
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