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Selective N-alkylation of azoles via anion-binding catalysis

Award Number: F32GM156017
ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES
OPDIV: NIH
AWARD CLASS: DISCRETIONARY
AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS
PERIOD OF PERFORMANCE START DATE: 03/01/2026
PERIOD OF PERFORMANCE END DATE: 02/28/2029

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Selective N-alkylation of azoles via anion-binding catalysis - Project Summary Azoles are ubiquitous amongst bioactive molecules, present in approximately one third of commercial pharmaceuticals. However, selective preparation of N-alkylated azoles is an outstanding synthetic challenge. As a result, stereochemistry and N-regioselectivity are often achieved through the separation of isomeric mixtures or introduced during de novo ring synthesis. This approach creates a significant synthetic barrier when evaluating analogs of bioactive molecules during drug discovery campaigns. Therefore, a selective method to install alkyl fragments on existing azoles is poised to advance the fields of chemical biology and medicinal chemistry. This proposal leverages anion-binding catalysis to induce enantio- and N-regioselectivity in azole alkylation. We will study how hydrogen-bond-donor catalysts engage azole nucleophiles through a network of noncovalent interactions to control selective nucleophile delivery. Aim 1. We are advancing an enantioconvergent SN1 reaction to form a-tertiary azoles. Aim 2. We are developing a novel method for N-regiocontrol to form the contra-thermodynamic azole product. The methods developed through this work will address long-standing challenges in azole chemistry, enabling the synthesis of medicinally relevant frameworks that are currently inaccessible. Additionally, the research plan will develop a deep understanding of the structural features required to engage azoles as competent nucleophiles in anion-abstraction catalysis, introducing a new class of nucleophiles to this approach. Beyond tackling a significant challenge in modern synthesis, I also designed my research plan to provide me with training in multiple important areas that I had limited exposure to in during my doctoral career. Through performing the proposed experiments, I will become proficient in asymmetric catalysis, supramolecular chemistry, carbohydrate chemistry, computational analysis, and mechanistic investigation. Furthermore, I will both enhance my existing synthetic repertoire through the synthesis of new catalyst architectures and become familiar with new experimental techniques such as measurement of enantioenrichment by HPLC. Therefore, the proposed research plan will prepare me with the skills I need to pursue an independent academic position.


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 = $75,052 )
2026	2026	PRESIDENT AND FELLOWS OF HARVARD COLLEGE	1033 MASSACHUSETTS AVE STE 3	CAMBRIDGE	MA	02138	MIDDLESEX	USA	Biomedical Research and Research Training	000	1	1/22/2026	NEW	$75,052
2026	2026	PRESIDENT AND FELLOWS OF HARVARD COLLEGE	1033 MASSACHUSETTS AVE STE 3	CAMBRIDGE	MA	02138	MIDDLESEX	USA	Biomedical Research and Research Training	001	1	1/22/2026	NEW	$0
														Subtotal = $75,052

Grand Total All Awards = $75,052

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Selective N-alkylation of azoles via anion-binding catalysis

Award Number: F32GM156017

ORGANIZATION: NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES

OPDIV: NIH

AWARD CLASS: DISCRETIONARY

AWARD ACTIVITY TYPE: FELLOWSHIP/SCHOLARSHIP/STUDENT LOANS

PERIOD OF PERFORMANCE START DATE: 03/01/2026

PERIOD OF PERFORMANCE END DATE: 02/28/2029

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