# Iron-Catalyzed Metathesis and Carbocation Cyclization Reactions

> **NIH NIH R01** · UNIVERSITY OF MICHIGAN AT ANN ARBOR · 2020 · $315,326

## Abstract

Project Summary/Abstract
The metathesis reaction between two alkenes represents a powerful tool for the formation of carbon-carbon
bonds, which has led to profound synthetic applications in a large variety of biologically active target structures.
The corresponding carbonyl-olefin metathesis reaction enables direct carbon-carbon bond construction,
however, currently available synthetic methods are severely limited by harsh reaction conditions or require the
use of stoichiometric metal alkylidene complexes as reagents. To date, no protocol of general synthetic utility
for catalytic carbonyl-olefin metathesis exists. The objective of the proposed research program is to identify a
chemical strategy that enables the catalytic carbonyl-olefin metathesis and related carbocyclization reactions
based on inexpensive and earth-abundant transition metals.
A distinctive feature of this new methodology is that it will provide a general and modular protocol for the
synthesis of a large variety of cyclic motifs incorporated in many ubiquitous chemical scaffolds and biologically
active complex molecules. Additionally, this new approach enables carbonyl-olefin metathesis reactions under
mild reaction conditions with high functional group tolerance. In particular, highly functionalized carbocycles
which all constitute core components of pharmacophores with a wide array of biological activities, will be
directly accessible in a single transformation. Such carbocycles include cyclopentenes, cyclohexenes, furans,
pyrans, pyridines and their analogs, indenes, napthalenes, spirocyclic, polycyclic as well as biaryl building
blocks. The utility of these new carbocyclization reactions catalyzed by earth-abundant transition metals will be
demonstrated by enabling the synthesis of biologically active target structures from simple, and readily
available starting materials. The compounds prepared within this research program will be incorporated into
the compound library maintained by the Center for Chemical Genomics (CCG) at the University of Michigan
and become part of high-throughput screening (HTS) approaches for biological research and novel drug
discovery projects.
In summary, the research proposed will establish the first general, catalytic carbonyl-olefin metathesis reaction
employing earth-abundant transition metals as a new tool for direct carbon-carbon bond construction which is
expected to have wide implications for the area of complex molecule synthesis.

## Key facts

- **NIH application ID:** 9989868
- **Project number:** 5R01GM118644-05
- **Recipient organization:** UNIVERSITY OF MICHIGAN AT ANN ARBOR
- **Principal Investigator:** Corinna Stefanie Schindler
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2020
- **Award amount:** $315,326
- **Award type:** 5
- **Project period:** 2016-08-01 → 2022-05-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/9989868

## Citation

> US National Institutes of Health, RePORTER application 9989868, Iron-Catalyzed Metathesis and Carbocation Cyclization Reactions (5R01GM118644-05). Retrieved via AI Analytics 2026-05-23 from https://api.ai-analytics.org/grant/nih/9989868. Licensed CC0.

---

*[NIH grants dataset](/datasets/nih-grants) · CC0 1.0*