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Mechanism-Based Design of Iron-Mediated Carbonyl-Olefin Metathesis Protocols

Award Number: R15GM128126
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)
PERIOD OF PERFORMANCE START DATE: 05/01/2018
PERIOD OF PERFORMANCE END DATE: 08/31/2025

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Mechanism-Based Design of Iron-Mediated Carbonyl-Olefin Metathesis Protocols - Project Summary Lewis acid-activation of carbonyl-containing substrates is broadly utilized in organic synthesis. However, iron(III)- catalyzed carbonyl-olefin ring-closing metathesis employs reactivity not typically observed in Lewis acid- facilitated reactions. Using our detailed understanding of the mechanistic behavior of the iron catalyst in carbonyl- olefin metathesis, this proposal intends to apply this knowledge in the rational design of new metathesis catalysts. It is our hypothesis that, via appropriate ligand support, the reaction can be performed in solvents preferred in the production of pharmaceuticals, the natural, inhibitory mechanism can be prevented, and chemists will be able to select for a specific transition state in the turnover-limiting step. To facilitate catalyst design, synthetic, spectroscopic, kinetic, and computational techniques will be employed to observe the chemical space created by the incorporation of ligands, measuring their impact on the resting state of the catalytic cycle, as well as the turnover-limiting step. Further, substrate itself acts as a reactivity-directing ligand. Therefore, simple modifications to the carbonyl and olefin metathesis partners can not only change the operating mechanism, but dramatically alter reaction outcomes. Overall, these rigorous synthetic and mechanistic studies will employ the factors we have enumerated thus far to provide improved reaction outcomes, enhancing the use of carbonyl- olefin metathesis in the construction of medicinally important molecules.


Issue Date FY	Funding FY	Legal Entity Name	Legal Entity Address	Legal Entity City	Legal Entity State	Legal Entity Zip Code	Legal Entity COUNTY	Legal Entity COUNTRY	Assistance Listing	Award Code	Budget Year	Action Date	Action Type	Action Amount

Issue Date FY: 2026 ( Subtotal = -$22,525 )
2026	2021	LOYOLA UNIVERSITY OF CHICAGO	820 N MICHIGAN AVE	CHICAGO	IL	60611	COOK	USA	Biomedical Research and Research Training	000	2	4/1/2026	COMPETING CONTINUATION	-$22,525
														Subtotal = -$22,525

Issue Date FY: 2024 ( Subtotal = $0 )
2024	2021	LOYOLA UNIVERSITY OF CHICAGO	820 N MICHIGAN AVE	CHICAGO	IL	60611	COOK	USA	Biomedical Research and Research Training	000	2	9/25/2024	COMPETING CONTINUATION	$0
														Subtotal = $0

Issue Date FY: 2023 ( Subtotal = $0 )
2023	2018	LOYOLA UNIVERSITY OF CHICAGO	820 N MICHIGAN AVE	CHICAGO	IL	60611	COOK	USA	Biomedical Research and Research Training	000	1	11/23/2022	NEW	$0
														Subtotal = $0

Issue Date FY: 2022 ( Subtotal = $0 )
2022	2021	LOYOLA UNIVERSITY OF CHICAGO	1032 W SHERIDAN RD	CHICAGO	IL	60660	COOK	USA	Biomedical Research and Research Training	001	2	3/7/2022	COMPETING CONTINUATION	$19,681
2022	2018	LOYOLA UNIVERSITY OF CHICAGO	1032 W SHERIDAN RD	CHICAGO	IL	60660	COOK	USA	Biomedical Research and Research Training	000	1	3/7/2022	NEW	-$19,681
														Subtotal = $0

Issue Date FY: 2021 ( Subtotal = $403,593 )
2021	2021	LOYOLA UNIVERSITY OF CHICAGO	1032 W SHERIDAN RD	CHICAGO	IL	60660	COOK	USA	Biomedical Research and Research Training	001	2	8/30/2021	COMPETING CONTINUATION	$403,593
2021	2018	LOYOLA UNIVERSITY OF CHICAGO	1032 W SHERIDAN RD	CHICAGO	IL	60660	COOK	USA	Biomedical Research and Research Training	000	1	8/20/2021	NEW	$0
														Subtotal = $403,593

Issue Date FY: 2018 ( Subtotal = $403,639 )
2018	2018	LOYOLA UNIVERSITY OF CHICAGO	1032 W SHERIDAN RD	CHICAGO	IL	60660	COOK	USA	Biomedical Research and Research Training	000	1	4/11/2018	NEW	$403,639
														Subtotal = $403,639

Grand Total All Awards = $784,707

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Mechanism-Based Design of Iron-Mediated Carbonyl-Olefin Metathesis Protocols

Award Number: R15GM128126

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

PERIOD OF PERFORMANCE START DATE: 05/01/2018

PERIOD OF PERFORMANCE END DATE: 08/31/2025

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