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Formal One Carbon Deletion of Indoline Hemiaminals under Tautomeric Control to Access 2-Aminobenzyl Compounds
- Source :
- The Journal of Organic Chemistry; 20240101, Issue: Preprints
- Publication Year :
- 2024
-
Abstract
- Unprecedented tert-BuOK-mediated one carbon deletion of indoline hemiaminals has been achieved. This novel protocol provides an efficient synthetic tool for the construction of 2-aminobenzyl compounds with high chemoselectivity. In addition, functionalized 2-aminobenzyl compounds are difficult to make, for which few limited means of access currently exist. The key to success is the use of in situ generated Heyns rearrangement products (α-amino carbonyl compounds) as precursors for formal one carbon deletion.
Details
- Language :
- English
- ISSN :
- 00223263
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- The Journal of Organic Chemistry
- Publication Type :
- Periodical
- Accession number :
- ejs66773807
- Full Text :
- https://doi.org/10.1021/acs.joc.4c00884