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Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones
- Source :
- Journal of Organic Chemistry, Journal of Organic Chemistry, 2017, 82 (22), pp.11897-11902. ⟨10.1021/acs.joc.7b01623⟩, Journal of Organic Chemistry, American Chemical Society, 2017, 82 (22), pp.11897-11902. ⟨10.1021/acs.joc.7b01623⟩
- Publication Year :
- 2017
- Publisher :
- HAL CCSD, 2017.
-
Abstract
- This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.
- Subjects :
- 010405 organic chemistry
Chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Nitrene
Organic Chemistry
[CHIM.CATA]Chemical Sciences/Catalysis
010402 general chemistry
01 natural sciences
Combinatorial chemistry
0104 chemical sciences
Catalysis
Reagent
Organic chemistry
Stereoselectivity
Lewis acids and bases
Stoichiometry
ComputingMilieux_MISCELLANEOUS
Subjects
Details
- Language :
- English
- ISSN :
- 00223263 and 15206904
- Database :
- OpenAIRE
- Journal :
- Journal of Organic Chemistry, Journal of Organic Chemistry, 2017, 82 (22), pp.11897-11902. ⟨10.1021/acs.joc.7b01623⟩, Journal of Organic Chemistry, American Chemical Society, 2017, 82 (22), pp.11897-11902. ⟨10.1021/acs.joc.7b01623⟩
- Accession number :
- edsair.doi.dedup.....69db5102afcf46885889e441ca25c202