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Irreversible Oxy-2-azonia-Cope Rearrangements for the Synthesis of Functionalized Allyl α-Amino Acid Derivatives
- Source :
- European Journal of Organic Chemistry. 2014:2379-2385
- Publication Year :
- 2014
- Publisher :
- Wiley, 2014.
-
Abstract
- A general method to synthesize functionalized allyl α-amino acid derivatives through an irreversible oxy-2-azonia-Cope rearrangement is reported. In the presence of AlCl3, the reaction of imino ethyl glyoxalates with various β,γ-unsaturated ketones furnished the corresponding allyl α-amino acid derivatives. The key to the success of this method is the amide bond formation, which makes the rearrangement irreversible. This reaction system constitutes a new strategy for the synthesis of unusual allyl glycine derivatives, which are valuable synthetic intermediates. An efficient and operationally simple three-component version of this reaction was also performed.
Details
- ISSN :
- 1434193X
- Volume :
- 2014
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi...........c0add4ec78475e2ec132cd2293547a96