# Computational Investigations of Asymmetric Carbon-Carbon Bond Formation

> **NIH NIH F32** · UNIVERSITY OF CALIFORNIA LOS ANGELES · 2022 · $23,235

## Abstract

PROJECT SUMMARY
The asymmetric formation of carbon–carbon bonds is one of the greatest challenges in organic synthesis and is
an important transformation in the production of pharmaceuticals. Often, the development of these and other
reactions involves empirical screening of large sets of conditions in order to arrive at an efficient transformation.
Despite great progress in stereoselective organic synthesis, there remains a dearth of knowledge and
generalizable models of several of the most fundamental reactions in the field.
Computational chemistry has proven to be a versatile tool in the determination of mechanism and the
development of new chiral catalysts. Through the use of computational methods, we will study the mechanisms
and modes of stereoinduction in multiple transformations, with the goal of rationally designing new and more
selective catalysts. As a results of the proposed research, I will develop a method to build on computational
determination of stereoselectivity origins to predict superior asymmetric catalysts. This will lower the cost, time,
and environmental impact of synthetic methodology development.
Several categories of asymmetric carbon–carbon bond forming reactions will be studied computationally,
including [3+2] and [4+2] cycloadditions, nickel-catalyzed reductive cyclizations, and nickel-catalyzed cross-
electrophile couplings. Stereochemical models for reactions involving multiple classes of privileged chiral
scaffolds, including TADDOL ligands and bidentate nitrogen ligands, will be developed. In all of these reactions,
the precise identity of the catalyst has an important effect on stereochemical outcome and efficiency. By
developing a model supported by a wide range of data, the results of these studies will be extrapolated further
for the development of more efficient and potent synthetic methods. An understanding of the mechanisms of
these reactions, as well as the unique efficiency afforded by certain catalysts, will allow for the computational
prediction of more powerful and selective chiral catalysts. These catalysts will subsequently be synthesized in
the laboratory and applied to a selection of synthetic reactions in order to validate their effectiveness.

## Key facts

- **NIH application ID:** 10479795
- **Project number:** 5F32GM134709-02
- **Recipient organization:** UNIVERSITY OF CALIFORNIA LOS ANGELES
- **Principal Investigator:** Aneta Turlik
- **Activity code:** F32 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2022
- **Award amount:** $23,235
- **Award type:** 5
- **Project period:** 2021-05-01 → 2022-08-19

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10479795

## Citation

> US National Institutes of Health, RePORTER application 10479795, Computational Investigations of Asymmetric Carbon-Carbon Bond Formation (5F32GM134709-02). Retrieved via AI Analytics 2026-05-23 from https://api.ai-analytics.org/grant/nih/10479795. Licensed CC0.

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