One-step Preparation of N-Unprotected Aziridines from 2H-Azirines by Addition of Ketene Silyl Acetals Catalyzed by Lewis Acids
- 14 October 2021
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 51 (1), 9-12
- https://doi.org/10.1246/cl.210589
Abstract
The nucleophilic addition of ketene silyl acetals 2 into 2H-azirines 1 proceeded in the presence of Lewis acids such as InX3 or Sc(OTf)3 to give N-unprotected aziridines 3. The mild Lewis acidity of the catalyst is important for the achievement of this coupling. The generated aziridine 3 could then be transformed into either oxazolines or γ–amino carbonyls.Keywords
This publication has 39 references indexed in Scilit:
- Regioselectivity in the ring opening of non-activated aziridinesChemical Society Reviews, 2011
- Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium SaltsThe Journal of Organic Chemistry, 2011
- Catalytic aziridination of electron-deficient olefins with an N-chloro-N-sodio carbamate and application of this novel method to asymmetric synthesisChemical Communications, 2008
- Asymmetric Enamine CatalysisChemical Reviews, 2007
- Novel organic-solvent-free aziridination of olefins: Chloramine-T–I2 system under phase-transfer catalysis conditionsJournal of the Chemical Society, Perkin Transactions 1, 2001
- Catalytic and asymmetric aziridination of alkenes catalysed by a chiral manganese porphyrin complexChemical Communications, 1997
- Synthesis, crystal structure and catalytic activities of [RuIII(bbpc)(PPh3)Cl][H2bbpc = 1,2-bis(4-tert-butylpyridine-2-carboxamido)-4,5-dichlorobenzene]J. Chem. Soc., Dalton Trans., 1995
- Aziridination of alkenes catalysed by porphyrinirons: selection of catalysts for optimal efficiency and stereospecificityJournal of the Chemical Society, Perkin Transactions 2, 1988
- Induction asymétrique et réaction des α‐hydroxy‐oximes avec le bromure de phenylmagnésium. Synthéses stéreoselectives d'alcools aziridiniques et d'aza‐bicyclo[3.1.0]oxo‐2 oxaisothiazolidines‐1,2,3Journal of Heterocyclic Chemistry, 1980
- Studies on heterocyclic chemistry. Part X. Synthesis of aziridin-2-ylphosphonates by the thermally induced isomerization of isoxazoles in trialkyl phosphites. A related reaction of 2H-azirineJournal of the Chemical Society C: Organic, 1971