Department Seminar, Dr. Thierry Ollevier, Universite Laval, Thursday, March 9, 1:30pm
Mar 9, 2023
1:30PM to 2:30PM
Date(s) - 09/03/2023
1:30 pm - 2:30 pm
Title: Recent Advances in the Use of Chiral Iron Bipyridines for Asymmetric Catalysis
Date: Thursday, March 9, 2023
Room: ABB 165
Zoom: please email firstname.lastname@example.org for Zoom details
Hosts: Daniel Hrabowyj and Jim McNulty
Abstract: The objective of our research program is the development of new synthetic methods, with emphasis on catalytic and enantioselective procedures for the simple preparation of molecules. Our program targets major advancements in green chemistry, which is an area of major strategic and industrial importance. Iron-derived Lewis acids have been developed as green catalysts for asymmetric synthesis. Chiral iron complexes have been employed in selected asymmetric C–C, C–N, and C–S bond-forming reactions, such as the Mukaiyama aldol, epoxide opening, thia-Michael and Diels-Alder reactions.1 As we focused our interest on the ligand design of 2,2?-bipydiols, both steric and electronic properties of these ligands were tackled.2 The synthesis of a bulky (S,S)-2,2?-bipyridine-a,a?-1-Adamantyl-diol ligand was developed and its synthetic value was demonstrated in selected FeII/III-catalyzed benchmark reactions in terms of chiral induction when compared to other 2,2?-bipydiol analogs. Also, we have been the first to develop an efficient chiral C2-symmetric 2,2?-bipydiol ligand possessing a CF3 group in the a,a?-positions. These results contribute to the development of iron catalysis for asymmetric synthesis.
1. (a) Li, M.; Carreras, V.; Jalba, A.; Ollevier, T. Org. Lett. 2018, 20, 995. (b) Lauzon, S.; Keipour, H.; Gandon, V.; Ollevier, T. Org. Lett. 2017, 19, 6324. (c) Ollevier, T.; Plancq., B. Chem. Commun. 2012, 48, 2289.
2. (a) Lauzon, S.; Schouwey, L.; Ollevier, T. Org. Lett. 2022, 24, 1116. (b) Lauzon, S.; Caron, L.; Ollevier, T. Org. Chem. Front. 2021, 8, 2242. (c) Lauzon, S.; Ollevier, T. Chem. Commun. 2021, 57, 11025. (d) Lauzon, S.; Ollevier, T. Chem. Sci. 2022, 13, 10985.