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Asymmetric Synthesis of Nitrogen Heterocycles

Award Number: R01GM080442
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: SCIENTIFIC/HEALTH RESEARCH (INCLUDES SURVEYS)

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Project Summary/Abstract Nitrogen is the fourth most common element in pharmaceuticals and biologically active molecules, after only C, H and O. Its incidence greatly eclipses that of other important elements such as S and F. Methods to introduce nitrogen moieties into commonly available starting materials would provide practitioners with rapid access to more complex structures. We have had a long-standing interest in assembling nitrogen heterocycles due to their prevalence and importance. Our work began with approaches to construction of bicyclic structures using cycloaddition chemistry. Over time, it evolved to using C–H activation and generating monocyclic structures. With an eye towards increased utility and impact, we have continued to evolve our approach to using increasingly abundant alkene partners with broadly versatile amine derivatives for the continued synthesis of nitrogen heterocycles as well as acyclic scaffolds. Thus, this competitive renewal is focused on several complementary venues: Aim 1: Stereospecific Catalytic Alkene Difunctionalization Reactions. Alkenes are among the most ubiquitous starting materials available. The delivery of two functionalities across the stereochemically defined alkene allows access to complementary diastereomers if the reaction is stereospecific. We will develop a suite of difunctionalization reactions including carboamination, carbocarbation and related transformations. Where possible we will use unfunctionalized precursors in such a way to increase utility and ease of execution. Aim 2: Chemoselective Coupling of Alkenes and Nitrogen Electrophiles. We will extend alkene functionalization chemistry to convert simple ¿-olefins directly into pyrrolidines, piperidines and allylic amine derivatives, functionalizing not just the alkene itself but also the allylic, homoallylic and bis-homoallylic positions. Aim 3: Design of Artificial Metalloenzymes for Enhanced Reactivity and Asymmetric Catalysis. Many of these reactions create chiral products. We will control the absolute stereochemistry of the transformations with novel metalloenzymes derived from transition metal catalysts docked within monomeric streptavidin protein scaffolds.


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: 2023 ( Subtotal = $332,563 )
2023	2023	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	202 LOW LIBRARY 535 W 116 ST MC 4309,	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	17	8/15/2023	COMPETING CONTINUATION	$332,563
														Subtotal = $332,563

Issue Date FY: 2022 ( Subtotal = $381,033 )
2022	2022	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	202 LOW LIBRARY 535 W 116 ST MC 4309,	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	16	8/26/2022	NON-COMPETING CONTINUATION	$316,345
2022	2022	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	202 LOW LIBRARY 535 W 116 ST MC 4309,	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	001	16	8/30/2022	SUPPLEMENT FOR EXPANSION	$64,688
														Subtotal = $381,033

Issue Date FY: 2021 ( Subtotal = $427,763 )
2021	2021	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	002	15	8/18/2021	SUPPLEMENT FOR EXPANSION	$86,249
2021	2021	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	001	15	8/17/2021	NON-COMPETING CONTINUATION	$319,950
2021	2021	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	14	5/20/2021	SUPPLEMENT FOR EXPANSION	$21,564
														Subtotal = $427,763

Issue Date FY: 2020 ( Subtotal = $323,451 )
2020	2020	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	002	14	8/25/2020	NON-COMPETING CONTINUATION	$323,451
2020	2019	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	001	13	5/5/2020	COMPETING CONTINUATION	$0
2020	2018	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	12	5/5/2020	NON-COMPETING CONTINUATION	$0
														Subtotal = $323,451

Issue Date FY: 2019 ( Subtotal = $346,851 )
2019	2019	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	13	7/29/2019	COMPETING CONTINUATION	$346,851
														Subtotal = $346,851

Issue Date FY: 2018 ( Subtotal = $299,784 )
2018	2018	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	000	12	8/29/2018	NON-COMPETING CONTINUATION	$299,784
														Subtotal = $299,784

Issue Date FY: 2017 ( Subtotal = $299,784 )
2017	2017	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	002	11	8/21/2017	NON-COMPETING CONTINUATION	$299,784
2017	2016	TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK, THE	116TH AND BDWY	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	001	10	2/15/2017	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$138,650
2017	2015	COLORADO STATE UNIVERSITY	601 S HOWES ST	FORT COLLINS	CO	80521	LARIMER	USA	Biomedical Research and Research Training	000	9	2/15/2017	COMPETING CONTINUATION	-$138,650
														Subtotal = $299,784

Issue Date FY: 2016 ( Subtotal = $299,784 )
2016	2016	COLUMBIA UNIVERSITY	615 WEST 131ST ST, 4TH FLOOR	NEW YORK	NY	10027	NEW YORK	USA	Biomedical Research and Research Training	001	10	9/15/2016	CHANGE OF GRANTEE / TRAINING INSTITUTION / AWARDING INSTITUTION	$299,784
2016	2015	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	805232002	LARIMER	USA	Biomedical Research and Research Training	000	9	9/15/2016	COMPETING CONTINUATION	$0
														Subtotal = $299,784

Issue Date FY: 2015 ( Subtotal = $278,674 )
2015	2015	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	9	8/19/2015	COMPETING CONTINUATION	$278,674
														Subtotal = $278,674

Issue Date FY: 2014 ( Subtotal = $275,032 )
2014	2014	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	8	8/14/2014	NON-COMPETING CONTINUATION	$275,032
														Subtotal = $275,032

Issue Date FY: 2013 ( Subtotal = $281,522 )
2013	2013	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	001	7	8/29/2013	NON-COMPETING CONTINUATION	$270,514
2013	2013	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	6	3/19/2013	SUPPLEMENT FOR EXPANSION	$11,008
														Subtotal = $281,522

Issue Date FY: 2012 ( Subtotal = $272,165 )
2012	2012	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	6	9/5/2012	NON-COMPETING CONTINUATION	$272,165
														Subtotal = $272,165

Issue Date FY: 2011 ( Subtotal = $253,306 )
2011	2011	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	5	9/14/2011	COMPETING CONTINUATION	$253,306
2011	2010	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	001	4	9/14/2011	NON-COMPETING CONTINUATION	$0
														Subtotal = $253,306

Issue Date FY: 2010 ( Subtotal = $278,320 )
2010	2010	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	4	9/13/2010	NON-COMPETING CONTINUATION	$278,320
														Subtotal = $278,320

Issue Date FY: 2009 ( Subtotal = $299,566 )
2009	2009	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	001	3	8/31/2009	NON-COMPETING CONTINUATION	$289,905
2009	2009	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	2	8/20/2009	SUPPLEMENT FOR EXPANSION	$9,661
														Subtotal = $299,566

Issue Date FY: 2008 ( Subtotal = $235,923 )
2008	2008	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	2	8/28/2008	NON-COMPETING CONTINUATION	$235,923
														Subtotal = $235,923

Issue Date FY: 2007 ( Subtotal = $277,168 )
2007	2007	COLORADO STATE UNIVERSITY	UNIV SERVICES CENTER, ROOM 408	FORT COLLINS	CO	80523	LARIMER	USA	Biomedical Research and Research Training	000	1	9/21/2007	NEW	$277,168
														Subtotal = $277,168

Grand Total All Awards = $5,162,689

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Asymmetric Synthesis of Nitrogen Heterocycles

Award Number: R01GM080442

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

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

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