Data from: Organocatalytic enantioselective addition of 3-aryloxindoles to ethenesulfonyl fluoride
Data files
Dec 01, 2025 version files 54.66 MB
-
compound_17.zip
1.91 MB
-
compound_2a.zip
2.08 MB
-
compound_2b.zip
1.88 MB
-
compound_2c.zip
1.90 MB
-
compound_2d.zip
1.84 MB
-
compound_2e.zip
1.96 MB
-
compound_2f.zip
1.85 MB
-
compound_2g.zip
1.83 MB
-
compound_2h.zip
1.83 MB
-
compound_2i.zip
1.84 MB
-
compound_2j.zip
1.87 MB
-
compound_2k.zip
1.87 MB
-
compound_2l.zip
1.84 MB
-
compound_2m.zip
1.86 MB
-
compound_2n.zip
1.96 MB
-
compound_2o.zip
1.86 MB
-
compound_2p.zip
1.85 MB
-
compound_2q.zip
1.86 MB
-
compound_2r.zip
1.87 MB
-
compound_2s.zip
1.85 MB
-
compound_2t.zip
1.83 MB
-
compound_2u.zip
1.85 MB
-
compound_2v.zip
1.88 MB
-
compound_2w.zip
1.82 MB
-
compound_2x.zip
1.74 MB
-
compound_2y.zip
2.06 MB
-
compound_3.zip
1 MB
-
compound_4.zip
1 MB
-
compound_5.zip
1.06 MB
-
compound_6.zip
950.46 KB
-
compound_7.zip
1.85 MB
-
README.md
3.58 KB
Abstract
We report the synthesis of chiral sulfonyl fluorides bearing a carbon quaternary stereocenter. A commercially available organocatalyst (DHQD)2AQN 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.
1H NMR, 13C NMR, and HRMS spectra are used to describe the structure of all new compounds prepared in the publication: Organocatalytic Enantioselective Addition of 3-Aryloxindoles to Ethenesulfonyl Fluoride.
HPLC traces are used to determine the enantiomeric excesses of chiral compounds synthesized in this publication in Organic Letters, (acs.orglett.5c04026) https://doi.org/10.1021/acs.orglett.5c04026
Description of the data and file structure
Data for each compound are included in a folder named with the compound number designated in the manuscript and/or SI, as “compound number.zip”:
- compound_2a.zip
- compound_2b.zip
- compound_2c.zip
- compound_2d.zip
- compound_2e.zip
- compound_2f.zip
- compound_2g.zip
- compound_2h.zip
- compound_2i.zip
- compound_2j.zip
- compound_2k.zip
- compound_2l.zip
- compound_2m.zip
- compound_2n.zip
- compound_2o.zip
- compound_2p.zip
- compound_2q.zip
- compound_2i.zip
- compound_2j.zip
- compound_2k.zip
- compound_2l.zip
- compound_2m.zip
- compound_2n.zip
- compound_2q.zip
- compound_2r.zip
- compound_2s.zip
- compound_2t.zip
- compound_2u.zip
- compound_2v.zip
- compound_2w.zip
- compound_2x.zip
- compound_2y.zip
- compound_2z.zip
- compound_3.zip
- compound_4.zip
- compound_5.zip
- compound_6.zip
- compound_7.zip
- compound_17.zip
Each zip folder contains three sub-folders containing data for NMR (named as number_NMR), HRMS (named as number_HRMS), and HPLC (named as number_HPLC), respectively, for the compound indicated in the file name. Subfolder NMR includes files with the extension ".mnova" that contain acquisition and processing parameters and spectrum data for different nuclei named as "number_1HNMR", "number_13CNMR," and "number_19FNMR", respectively. Data in the JCAMP-DX open file format are also provided within each NMR sub-folder. These files are named in a similar way with the extension ".jcamp". Accessing this data will allow users to view NMR spectra interactively.
Subfolder HRMS contains data for High Resolution Mass Spectra carried out in the ESI+ technique, which provides the exact molecular mass and formula for the corresponding compounds. Files are in PDF format.
Subfolder HPLC contains traces of High Performance Liquid Chromatography analysis corresponding to chiral compounds (file named as "number_HPLC_EN") and their racemic forms (file named as "number_HPLC_RAC"). Files are in PDF format.
Abbreviations used are as follows:
NMR: nuclear magnetic resonance
HRMS: High-resolution Mass Spectra
HPLC: High Performance Liquid Chromatography
SI: supporting information (meaning, Supplementary Materials document)
File structures.pdf contains the structures of the reported compounds 2-7 and 17
Sharing/access Information
NMR and HPLC traces data will be available as images in the SI for this manuscript. X-ray data for compound 2e are available free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service. Deposition number CCDC 2489843
Code/Software
Processed files with extension .mnova are ready to be viewed in MestReNova. Files with extension .jcamp can be read and processed with unlicensed software such as JSpecView, ACD/Labs NMR Processor, or free online viewers such as NMRium
