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Harnessing Alkyl Amines and Alkyl Alcohols in Cross-Coupling Reactions

Award Number: R35GM131816
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: 06/01/2019
PERIOD OF PERFORMANCE END DATE: 05/31/2029

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Harnessing Alkyl Amines and Alkyl Alcohols in Cross-Coupling Reactions - The discovery of new medicines requires the synthesis and evaluation of new molecules, and the incorporation of saturated atoms and three-dimensional (3D) shape is increasingly important in advancing bioactive leads to medicines. Recognizing this need to incorporate saturated carbons, including stereocenters, this research will focus on the development of new cross-coupling reactions to enable efficient construction of bonds to saturated carbon atoms. These methods will rely on alkyl alcohol and amine derivatives as alkyl electrophiles, because they are widely available (including in enantioenriched form), offer outstanding diversity of alkyl fragments that is complementary to other alkylating agents, are easily prepared, and can be used in both early and late-stage functionalization strategies. All-carbon quaternary stereocenters and other fully substituted stereocenters are prevalent in bioactive natural products, but these motifs remain synthetically challenging to prepare in high enantiomeric purity, especially if they are not near a carbonyl or alkene. On the other hand, tertiary alcohols are readily prepared in exceptional enantiomeric excess (ee), making them ideal substrates for stereospecific cross-coupling reactions. Building on strong preliminary results, this program will develop a suite of methods to deliver highly enantioenriched products from tertiary benzylic alcohol derivatives. These efforts will be bolstered by mechanistic studies to understand and rationally optimize challenging steps in these catalytic processes. Primary alkyl amines comprise an extremely diverse feedstock class, extending from simple building blocks to pharmaceutical intermediates to biomolecules. By activating them as Katritzky pyridinium salts, the PI’s group was the first to show that these ubiquitous starting materials can be used as alkyl electrophiles in nickel-catalyzed cross-coupling reactions. This program will now develop new deaminative cross-couplings to provide efficient access to a tremendous diversity of products, meeting needs in medicinal chemistry efforts for pharmaceutical discovery. The successful development of this research will establish novel methods to deliver 3D molecules with potential bioactivity from readily available precursors. It will also change the way that chemists use alcohols and amines in synthesis. The ultimate goal is to develop cross-coupling methods for forging bonds to C(sp3) atoms that are as useful for the preparation of bioactive molecules as those long known for C(sp2) atoms. By enabling new methods for the synthesis of novel, potentially bioactive molecules, this research will advance the discovery of new molecules for the study and treatment of disease.


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: 2025 ( Subtotal = $423,631 )
2025	2025	UNIVERSITY OF DELAWARE	550 S COLLEGE AVE	NEWARK	DE	19713	NEW CASTLE	USA	Biomedical Research and Research Training	002	7	5/2/2025	NON-COMPETING CONTINUATION	$423,631
2025	2024	UNIVERSITY OF DELAWARE	550 S COLLEGE AVE	NEWARK	DE	19713	NEW CASTLE	USA	Biomedical Research and Research Training	000	6	11/11/2024	COMPETING CONTINUATION	$0
2025	2023	UNIVERSITY OF DELAWARE	550 S COLLEGE AVE	NEWARK	DE	19713	NEW CASTLE	USA	Biomedical Research and Research Training	001	5	2/11/2025	NON-COMPETING CONTINUATION	$0
														Subtotal = $423,631

Issue Date FY: 2024 ( Subtotal = $460,319 )
2024	2024	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	6	4/19/2024	COMPETING CONTINUATION	$460,319
														Subtotal = $460,319

Issue Date FY: 2023 ( Subtotal = $487,681 )
2023	2023	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	001	5	5/16/2023	SUPPLEMENT FOR EXPANSION	$16,078
2023	2023	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	5	5/12/2023	NON-COMPETING CONTINUATION	$385,551
2023	2023	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	002	5	6/26/2023	SUPPLEMENT FOR EXPANSION	$86,052
														Subtotal = $487,681

Issue Date FY: 2022 ( Subtotal = $445,281 )
2022	2022	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	001	4	5/11/2022	SUPPLEMENT FOR EXPANSION	$59,730
2022	2022	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	4	5/10/2022	NON-COMPETING CONTINUATION	$385,551
														Subtotal = $445,281

Issue Date FY: 2021 ( Subtotal = $433,785 )
2021	2021	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	3	5/27/2021	NON-COMPETING CONTINUATION	$385,551
2021	2021	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	001	3	8/25/2021	SUPPLEMENT FOR EXPANSION	$48,234
														Subtotal = $433,785

Issue Date FY: 2020 ( Subtotal = $385,458 )
2020	2020	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	2	5/18/2020	NON-COMPETING CONTINUATION	$385,458
														Subtotal = $385,458

Issue Date FY: 2019 ( Subtotal = $333,206 )
2019	2019	UNIVERSITY OF DELAWARE	220 HULLIHEN HALL	NEWARK	DE	19716	NEW CASTLE	USA	Biomedical Research and Research Training	000	1	5/9/2019	NEW	$333,206
														Subtotal = $333,206

Grand Total All Awards = $2,969,361

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Harnessing Alkyl Amines and Alkyl Alcohols in Cross-Coupling Reactions

Award Number: R35GM131816

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: 06/01/2019

PERIOD OF PERFORMANCE END DATE: 05/31/2029

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