# Organocatalytic Practical Synthesis of Deuterated Building Blocks and Biologically Important Structures

> **NIH NIH R01** · UNIVERSITY OF ARIZONA · 2020 · $280,684

## Abstract

Project Summary
 The frustrating complexity of deuteration chemistry, a very limited number of deuterated building blocks
available and high cost of making them hamper access to highly sought deuterated bioactive molecules.
Therefore, practical synthesis of versatile deuterated building blocks and `privileged' structures will facilitate
the construction of deuterated molecules of interest for their biological studies and drug discovery. We wish
to develop a new aminocatalytic activation mode termed `ammonium catalysis' for deuterated molecule
synthesis. We challenge the dogma of amine moieties in adducts resulting from nucleophilic additions to
iminum ions can serve as leaving groups in ensuing reactions. In situ release of the presumed amine from
the addition products will create a new scenario for aminocatalytic direct functionalization of aldehydes. It
will be demonstrate that a number of unprecedented efficient catalytic cascade reactions will be realized by
the new organic catalysts and new reactivities. These cascade processes produce a fascinating array of
highly valued novel complex `privileged' benzopyrans and hydroquinolines with regioselective
incorporation of deuterium at metabolically labile sites. In addition, the first binary photo- and
organo-catalytic formylation reaction and NHC carbene promoted H/D exchange process with simple
non-deuterated aldehydes will be developed for low cost synthesis of fundamentally important
deuterated aldehydes and enals. Furthermore, practical chiral amine-catalyzed enantioselective H/D
exchange-α-functionalization cascade reactions for synthesis of chiral deuterated highly valued building
blocks such as (amino)sugars, amino acids, alcohols, amines etc. will be developed. Finally, new
trimethylsulfoxonium iodide promoted CH3/CD3 exchange reactions for synthesis of synthetically and
medicinally valued deuterated methyl, cyclopropanes, epoxides, aziridines and therapeutics will be
accomplished. These deuterated building blocks and molecular architectures and drugs serve as
valuable tools for biomedical researchers to use for biomolecule constructions and biological and drug
discovery studies.

## Key facts

- **NIH application ID:** 9918424
- **Project number:** 5R01GM125920-04
- **Recipient organization:** UNIVERSITY OF ARIZONA
- **Principal Investigator:** WEI WANG
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2020
- **Award amount:** $280,684
- **Award type:** 5
- **Project period:** 2018-06-10 → 2022-03-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/9918424

## Citation

> US National Institutes of Health, RePORTER application 9918424, Organocatalytic Practical Synthesis of Deuterated Building Blocks and Biologically Important Structures (5R01GM125920-04). Retrieved via AI Analytics 2026-05-26 from https://api.ai-analytics.org/grant/nih/9918424. Licensed CC0.

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