# Versatile complex amine synthesis via aziridinium ylides and 2-amidoallyl cations

> **NIH NIH R01** · UNIVERSITY OF WISCONSIN-MADISON · 2020 · $185,500

## Abstract

Project Summary/Abstract:
 Efficient access to molecules of importance to human health has long driven the development of innovative
synthetic methods. In recent years, greater emphasis has been placed on explorations of stereochemically
complex molecular space not well-represented in typical compound screening libraries. In this context, N-
heterocycles and aminated carbocycles are particularly attractive targets, as they are prevalent in drugs,
natural products, biomolecules, and ligands. A unified and modular platform capable of rapid, flexible
transformations of a simple set of precursors into azetidines, pyrrolidines, piperidines and amine-bearing
carbocycles could speed drug discovery processes in complex amine chemical space. Our premise is that
developing general, stereoselective routes to aziridinium ylides and 2-amidoallyl cations, coupled with the
ability to divert reactivity of these key intermediates along multiple pathways, will provide a versatile approach
to diverse, densely functionalized stereochemically complex N-heterocycles comprising useful bioactive
chemical space.
 In addition to the development of new synthetic methods, biological testing of chemical space unlocked by our
proposed work is critical to its long-term significance. Our program centered on new oxidative allene amination
methods for the synthesis of densely functionalized and heavily substituted amine motifs has yielded ~500
novel amines that have been submitted to the Eli Lilly Open Innovation Drug Discovery (OIDD) program, as
well as other academic and industrial collaborators. Promising results showing a broad range of bioactivities in
the amine space covered by this preliminary library. This proposal aims to add even more powerful and
versatile methods for the syntheses of complex amines from a set of modular, simple building blocks. All new
compounds synthesized in the course of these studies will be submitted for screening through OIDD, the UW-
Madison Medicinal Chemistry Center and other academic and industrial programs.

## Key facts

- **NIH application ID:** 10133877
- **Project number:** 3R01GM132300-02S1
- **Recipient organization:** UNIVERSITY OF WISCONSIN-MADISON
- **Principal Investigator:** Jennifer Marie Schomaker
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2020
- **Award amount:** $185,500
- **Award type:** 3
- **Project period:** 2019-05-01 → 2023-03-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10133877

## Citation

> US National Institutes of Health, RePORTER application 10133877, Versatile complex amine synthesis via aziridinium ylides and 2-amidoallyl cations (3R01GM132300-02S1). Retrieved via AI Analytics 2026-05-23 from https://api.ai-analytics.org/grant/nih/10133877. Licensed CC0.

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