# Development of a photoinduced, copper-catalyzed, enantioconvergent synthesis of unnatural amino acids

> **NIH NIH F32** · CALIFORNIA INSTITUTE OF TECHNOLOGY · 2020 · $64,926

## Abstract

ABSTRACT
β,β-Disubstituted-α-amino acids and α-aminoboronic acids are two classes of unnatural α-amino acids that are
present in pharmaceuticals used to treat conditions ranging from diabetes to cancer. There is considerable room
for improvement on existing methods for the preparation of these two classes of unnatural amino acids, as they
are largely dependent on diastereoselective synthesis with a stoichiometric amount of a chiral auxiliary. This
proposal outlines a research plan to develop a new asymmetric, photoinduced, copper-catalyzed methodology
to synthesize β,β-disubstituted-α-amino acids and α-aminoboronic acids from racemic of α-malonyl and α-boryl
NHP esters, respectively. Here, the chiral copper catalyst in combination with blue-LED irradiation will mediate
the decarboxylation of NHP esters and their subsequent enantioselective Csp3-N cross-coupling with phthalimide,
efficiently used as the source of protected amine. The proposed reaction will not generate any stoichiometric
waste, other than CO2, in the reaction itself, and will not require an exogenous precious metal photocatalyst to
initiate the reaction. The utility of this method will be explored through the synthesis of an array of hindered
unnatural α-amino acids and alkyl substituted α-aminoboronic acids, including new variants that have never been
synthesized before.

## Key facts

- **NIH application ID:** 9889808
- **Project number:** 5F32GM131595-02
- **Recipient organization:** CALIFORNIA INSTITUTE OF TECHNOLOGY
- **Principal Investigator:** Suzanne Marie Batiste
- **Activity code:** F32 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2020
- **Award amount:** $64,926
- **Award type:** 5
- **Project period:** 2019-03-01 → 2021-02-28

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/9889808

## Citation

> US National Institutes of Health, RePORTER application 9889808, Development of a photoinduced, copper-catalyzed, enantioconvergent synthesis of unnatural amino acids (5F32GM131595-02). Retrieved via AI Analytics 2026-05-23 from https://api.ai-analytics.org/grant/nih/9889808. Licensed CC0.

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