Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 13, Pages 6748-6763Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00895
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- Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan
- JSPS KAKENHI [JP26410048]
- Nanotechnology Platform Program of MEXT, Japan
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Catalytic cyclization of amides of ethenetricarboxylate bearing ether and acetal groups has been examined. The reaction of the amides bearing cyclic ether and acetal in groups the presence of Lewis acid such as Sc(OTf)(3) gave spirocyclic piperidine derivatives as major products. The cydized products may be formed via intramolecular hydride transfer. The reaction mechanism was examined by the DFT calculations. The scope and limitations of the hydride transfer/cyclization reactions of amides of ethenetricarboxylates was investigated, and morpholine formation by intramolecular oxy-Michael addition was also found.
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