# Catalytic Asymmetric Route to Enantioenriched Cyclic Allenes and a Nickel-catalyzed Dynamic Kinetic Resolution of Cyclic Allenes

> **NIH NIH F31** · UNIVERSITY OF CALIFORNIA LOS ANGELES · 2021 · $37,766

## Abstract

Highly functionalized heterocycles are important motifs in pharmaceuticals. Although there have been
many noteworthy advances in synthetic organic methodologies, the efficient synthesis of enantioenriched
heterocycles remains an ongoing challenge in the field. The primary goal of this proposal is to access
enantioenriched compounds utilizing heterocyclic allene intermediates. Cyclic allenes have been avoided
historically due to their high reactivity. However, the proposed research seeks to harness cyclic allenes for the
efficient construction of complex scaffolds. Moreover, the inherent chirality of cyclic allenes opens opportunities
to access enantioenriched adducts. The manipulation of heterocyclic allenes in a controlled manner would offer
new tactics for the synthesis of enantioenriched, complex heterocycles.
 This proposal includes two strategies that utilize heterocyclic allenes to generate enantioenriched
products. In Aim 1, an asymmetric, catalytic synthesis of oxacyclic allene precursors will be optimized to
ultimately enable facile access to enantioenriched oxacyclic allenes. An investigation into the ability to transfer
stereochemical information from the allene precursor all the way to enantioenriched cycloadducts will be
described. The studies in Aim 2 will allow access to enantioenriched heterocycles via a transition metal-
catalyzed dynamic kinetic resolution of heterocyclic allenes. Optimization of the transformation and exploration
of the substrate scope is described. These studies would ultimately demonstrate the utility of strained cyclic
allenes in asymmetric synthesis.

## Key facts

- **NIH application ID:** 10218217
- **Project number:** 5F31GM134625-03
- **Recipient organization:** UNIVERSITY OF CALIFORNIA LOS ANGELES
- **Principal Investigator:** Rachel Knapp
- **Activity code:** F31 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2021
- **Award amount:** $37,766
- **Award type:** 5
- **Project period:** 2019-08-01 → 2022-06-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10218217

## Citation

> US National Institutes of Health, RePORTER application 10218217, Catalytic Asymmetric Route to Enantioenriched Cyclic Allenes and a Nickel-catalyzed Dynamic Kinetic Resolution of Cyclic Allenes (5F31GM134625-03). Retrieved via AI Analytics 2026-05-24 from https://api.ai-analytics.org/grant/nih/10218217. Licensed CC0.

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