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Synthesis of Octahydro- and Decahydroquinolines by a One-Pot Cascade Reaction of Tetrasubstituted Enecarbamate
- Source :
- Organic Letters. 19(18):4762-4765
- Publication Year :
- 2017
- Publisher :
- American Chemical Society, 2017.
-
Abstract
- A transition-metal-catalyzed cyclopropanation followed by ring opening was investigated for the synthesis of octahydroquinolines 4 and decahydroquinolines 5 having a quaternary carbon center at the angular position, which are core structures of the fawcettimine-type alkaloids. A tandem reaction was also established for the synthesis of decahydroquinolines 5 and the tricyclic compound 6 through an iminium ion intermediate, readily produced by acidic treatment of cyclopropane 2.
- Subjects :
- 010405 organic chemistry
Chemistry
Cyclopropanation
Organic Chemistry
Iminium
010402 general chemistry
Ring (chemistry)
01 natural sciences
Biochemistry
0104 chemical sciences
Cyclopropane
chemistry.chemical_compound
Cascade reaction
Organic chemistry
Physical and Theoretical Chemistry
Quaternary carbon
Subjects
Details
- Language :
- English
- ISSN :
- 15237060
- Volume :
- 19
- Issue :
- 18
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....c0ee3505c3d0d4f5d421393f2cc34ae7