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Synthesis of C4-Aminated Indoles via a Catellani and Retro-Diels–Alder Strategy
- Source :
- Journal of the American Chemical Society. 141:9731-9738
- Publication Year :
- 2019
- Publisher :
- American Chemical Society (ACS), 2019.
-
Abstract
- Highly functionalized 4-aminoindoles were synthesized via the three-component cross-coupling of o-iodoaniline, N-benzoyloxyamines, and norbornadiene. The Catellani and retro-Diels-Alder strategy was used in this domino process. o-Iodoaniline, with electron-donating and sterically hindered protecting groups, made the reaction selective toward o-C-H amination. On the basis of density functional theory calculations, the intramolecular Buchwald coupling of this reaction underwent a dearomatization and a 1,3-palladium migration process. The reasons for the control of the chemical selectivity by the protecting groups are given. Moreover, synthetic applications toward 4-piperazinylindole and a GOT1 inhibitor were realized.
- Subjects :
- Steric effects
Norbornadiene
General Chemistry
010402 general chemistry
01 natural sciences
Biochemistry
Combinatorial chemistry
Catalysis
0104 chemical sciences
chemistry.chemical_compound
Colloid and Surface Chemistry
chemistry
Intramolecular force
Diels alder
Domino process
Selectivity
Amination
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 141
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....2bed4ada93885f290e3a3b69b24f9ad7