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Lewis Acid-Catalyzed Carbofunctionalization of Uncommon C,N-Diacyliminium Ions: Controlling Regio- and Enantioselectivity
- Source :
- Organic Letters. 23:7834-7838
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- The tricyclic azepino[1,2-a]indole acetates 7, readily accessible by visible-light-driven catalytic photooxygenation of cyclohepta[b]indoles 1, are convenient precursors to novel and uncommon cyclic C,N-diacyliminium ions 3. We report here the first Lewis acid-catalyzed C-C bond forming reactions of these species with TMSCN and silyl enol ethers as nucleophiles and utilizing TIPSOTf as well as Sc(OTf)3 as catalysts. Employing Sc(OTf)3/pybox complexes as a chiral catalyst system, regio- and enantioselective asymmetric alkylations with silyl enol ethers were achieved.
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 23
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi...........8e800af56e00f73051cbae900039678f