# Enantioselective α,α-Chlorofluorination of Sulfoxonium Ylides

**Authors:** Lucas G. Furniel, Kauê C. Capellaro, Viktor S. Câmara, Marcio Hayashi, Radell Echemendía, Camila B. Pinto, Ana B. A. M. Salata, Jackson A. L. Filho, Leandro W. Hantao, Javier Ellena, Antonio C. B. Burtoloso

PMC · DOI: 10.1021/acs.orglett.5c05062 · Organic Letters · 2026-01-28

## TL;DR

This paper reports a new method for creating chiral gem-dihalogenated compounds with high efficiency and enantioselectivity.

## Contribution

The paper introduces enantioselective α,α-chlorofluorination using chiral aminosulfoxonium ylides and fluorinating reagents from cinchona alkaloids.

## Key findings

- 25 examples of gem-dihalogenated compounds were synthesized with up to 90% yield.
- Enantioselectivity reached up to 96:4 er using chiral fluorinating reagents.
- The method includes bromochlorination and is derived from commercially available cinchona alkaloids.

## Abstract

The first examples
of enantioselective α,α-chlorofluorination
of α-carbonylsulfoxonium ylides are described. Herein, two modes
of reaction are explored, using chiral aminosulfoxonium ylides and
a chiral fluorinating reagent, prepared in situ from
commercially available cinchona alkaloids. Using these approaches,
25 examples of gem-dihalogenated compounds (including bromochlorination)
were obtained in good yields (up to 90%) and enantioselectivity (up
to 96:4 er).

## Full-text entities

- **Chemicals:** Sulfoxonium Ylides (-), cinchona alkaloids (MESH:D002930)

## Full text

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## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12887995/full.md

## References

44 references — full list in the complete paper: https://tomesphere.com/paper/PMC12887995/full.md

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Source: https://tomesphere.com/paper/PMC12887995