Organocatalyzed Intramolecular Cyclization of oxo-Michael Substrates
-
1
University of North Carolina at Greensboro, United States
The three-dimensional shape of a biologically active compound is essential for the activity of the molecule. Some pharmaceutical drugs are racemic mixtures of R and S enantiomers. However, one of the enantiomers may be the active component of the mixture, while the other enantiomer is inactive and could potentially cause adverse effects on human health. Hence, the need for innovative design of methodology to develop the synthesis of enantioenriched compounds. Our synthetic approach to these types of molecules is the asymmetric synthesis of enantioenriched building blocks that contain functional groups which undergo rapid transformation into an assortment of functionalities. With these variable functionalities, the chiral building blocks can be incorporated into complex enantioenriched molecules. We propose the novel activation of nitriles via a chiral Brønsted acid catalyzed intramolecular oxo-Michael reaction. Previous work in the Petersen group has found that binol based phosphoric acid organocatalysts are efficient and selective catalysts for the asymmetric intramolecular desymmetrization of hydroxy alcohols. This research project presents a novel approach to asymmetric synthesis via a hetero-Michael addition to oxo-Michael substrates. This approach will be accomplished utilizing a chiral Brønsted acid catalyst to activate the substrates towards an intramolecular cyclization.
Acknowledgements
I would like to thank Dr. Kimberly Petersen for affording me the opportunity to complete this research. I would also like to thank, the University of North Carolina at Greensboro and the National Institutes of Health NIH: R15(GM116041) for funding this research.
References
Lukas, H.; Jens, A.; Florian, B., Inner Workings of a Cinchona Alkaloid Catalyzed Oxa-Michael Cyclization: Evidence for a Concerted Hydrogen-Bond-Network Mechanism. Chemistry – A European Journal., 2013, 19 (7), 2311-2321.
Wilent, J.; Petersen, K., Enantioselective Desymmetrization of Diesters. J. Org. Chem., 2014, 79 (5), 2303–2307.
Keywords:
asymmetric synthesis,
Organocatalyis,
Bronsted acid catalysts,
Michael addition,
Oxo-michael addition reaction
Conference:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference , Orlando, Florida, United States, 17 Sep - 20 Sep, 2018.
Presentation Type:
Poster Presentation
Topic:
Organic Chemistry
Citation:
Haywood
R and
Petersen
KS
(2019). Organocatalyzed Intramolecular Cyclization of oxo-Michael Substrates.
Front. Chem.
Conference Abstract:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference .
doi: 10.3389/conf.fchem.2018.01.00034
Copyright:
The abstracts in this collection have not been subject to any Frontiers peer review or checks, and are not endorsed by Frontiers.
They are made available through the Frontiers publishing platform as a service to conference organizers and presenters.
The copyright in the individual abstracts is owned by the author of each abstract or his/her employer unless otherwise stated.
Each abstract, as well as the collection of abstracts, are published under a Creative Commons CC-BY 4.0 (attribution) licence (https://creativecommons.org/licenses/by/4.0/) and may thus be reproduced, translated, adapted and be the subject of derivative works provided the authors and Frontiers are attributed.
For Frontiers’ terms and conditions please see https://www.frontiersin.org/legal/terms-and-conditions.
Received:
16 Oct 2018;
Published Online:
17 Jan 2019.
*
Correspondence:
Dr. Kimberly S Petersen, University of North Carolina at Greensboro, Greensboro, United States, kspeters@uncg.edu