# Administrative Equipment Supplement for New Methods for Nitrogen and Oxygen Heterocycle Synthesis

> **NIH NIH R01** · STATE UNIVERSITY OF NEW YORK AT BUFFALO · 2021 · $45,161

## Abstract

Project Summary/Abstract
The efficient production of small organic molecules and chemical processes impacts pharmaceutical
research, both drug discovery and process chemistry. Chiral compounds make up a substantial portion
of bioactive small organic molecules. Their enantioselective synthesis minimizes use of chiral
separation technology, which can be time and resource intensive, and the production of undesired
enantiomers, which are often considered chemical waste. New copper-catalyzed alkene
difunctionalization reactions that enable efficient and stereoselective synthesis of chiral amine
derivatives and ethers, including saturated heterocycles, are being developed. The products of these
reactions readily map on to structures contained in bioactive organic small molecules such as natural
products and pharmaceuticals. In Aim 1, enantioselective aerobic copper-catalyzed alkene oxidative
difunctionalizations are being explored for the direct synthesis of 2-formyl pyrrolidines and 2-formyl
tetrahydrofurans. Application of these aerobic cyclizations to the streamlined synthesis of bioactive
natural products and small molecule intermediates useful to drug discovery will test the practical utility
of the methods. The focus of Aim 2 is the development of methods for the enantioselective synthesis
of chiral bridged bicyclic ketals and other saturated heterocycles that contain fully substituted carbon
stereocenters. A number of these transformations are enabled by a radical group transfer strategy.
Mechanistic aspects of these reactions will be explored, which will enable their rational optimization
and predictable application. The focus of Aim 3 is the development of copper-catalyzed 2- and 3-
component reactions that involve the coupling of alcohol and amine derivatives with styrenes or dienes,
and alkyl radicals formed in situ. Mechanistic aspects of these reactions, especially related to
stereoselectivity, will be investigated. Development of these chemical transformations will enable their
use in multi-step organic synthesis in drug discovery and chemical biology applications. Their invention
enables new options for synthetic organic chemists, which may enable diverse small molecule
candidates to be synthesized efficiently. Lessons learned in reaction engineering for efficiency and
selectivity should be applicable to the invention and development of related useful chemical processes.

## Key facts

- **NIH application ID:** 10380459
- **Project number:** 3R01GM078383-15S1
- **Recipient organization:** STATE UNIVERSITY OF NEW YORK AT BUFFALO
- **Principal Investigator:** Sherry R Chemler
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2021
- **Award amount:** $45,161
- **Award type:** 3
- **Project period:** 2006-07-01 → 2024-06-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10380459

## Citation

> US National Institutes of Health, RePORTER application 10380459, Administrative Equipment Supplement for New Methods for Nitrogen and Oxygen Heterocycle Synthesis (3R01GM078383-15S1). Retrieved via AI Analytics 2026-05-22 from https://api.ai-analytics.org/grant/nih/10380459. Licensed CC0.

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