Organocatalytic Enantioselective Addition of 3-Aryloxindoles to Ethenesulfonyl Fluoride
We report the synthesis of chiral sulfonyl fluorides bearing a carbon quaternary stereocenter. A commercially available organocatalyst (DHQD)<sub>2</sub>AQN enables the enantioselective addition of 3-substituted oxindoles to ethenesulfonyl fluoride (ESF), achieving excellent yields (27-99%) and enantioselectivities (89-99% ee) for 3-arylsubstituted oxindoles. This methodology shows high functional group tolerance, as demonstrated by successfully engaging halides, ethers, nitriles, acetals, ketals, or heteroaromatic substituents. The utility of the described products was proven by various synthetic transformations, including SuFEx reactions with complex biomolecules.
Authors
- Gonzalo Blay (ORCID: https://orcid.org/0000-0002-7379-6789)
- Marc Montesinos‐Magraner (ORCID: https://orcid.org/0000-0003-1713-6257)
- Carlos Vila (ORCID: https://orcid.org/0000-0001-9306-1109)
- Amparo Sanz‐Marco (ORCID: https://orcid.org/0000-0002-1729-598X)
- Iñaki Fernández-Yagüe
- Álvaro Castilla-Mocholí
Institutions
- Universitat de València (ES)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c04026
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Agencia Estatal de Investigación