# Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds

**Authors:** Julia Szymańska, Michał Rachwalski, Adam M. Pieczonka

PMC · DOI: 10.3390/molecules29143283 · 2024-07-11

## TL;DR

This paper describes a highly efficient asymmetric [3+2] cycloaddition reaction using chiral organophosphorus compounds to form specific stereoisomers.

## Contribution

The study introduces chiral aziridine-functionalized organophosphorus compounds as effective catalysts for asymmetric [3+2] cycloadditions.

## Key findings

- Three out of sixteen possible stereoisomers were formed in the reaction.
- Two stereoisomers were obtained in enantiomerically enriched or pure form.
- One product underwent epimerization under basic conditions.

## Abstract

The asymmetric [3+2] cycloaddition of azomethine ylides generated from the corresponding imino ester-to-trans-β-nitrostyrene catalysis by chiral aziridine-containing phosphines and phosphine oxides is described. Of the sixteen stereoisomers that could be formed as a result of the title reaction, three were formed, two of which were obtained in an enantiomerically enriched or pure form, and one in a racemic form. One of the products underwent epimerization under basic reaction conditions.

## Linked entities

- **Chemicals:** trans-β-nitrostyrene (PubChem CID 5284459), phosphine oxides (PubChem CID 166931)

## Figures

23 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11279481/full.md

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Source: https://tomesphere.com/paper/PMC11279481