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Direct Regioselective Reductive Allylation of Imines: Application to Synthesis of Oxazines with Halogenated Reagent
- Source :
- Organic Letters; December 2023, Vol. 25 Issue: 49 p8819-8823, 5p
- Publication Year :
- 2023
-
Abstract
- Oxazines are an important class of compounds in oxazine ligands and medical chemistry. Here, we describe a linear-selective allylation of imines with allyl electrophiles via cross-electrophile coupling reactions, followed by cyclization with halogenated reagents, providing a new strategy to afford oxazine compounds with a tetrasubstituted carbon center. Mechanistic studies indicate that α-amino carbanion, generated by successive single-electron transfer processes, is a key intermediate for nucleophile attack on π-allylpalladium in photoredox/palladium catalysis.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Volume :
- 25
- Issue :
- 49
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs64716942
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c03407