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- Title
Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro-Epoxyoxindoles.
- Authors
Pace, Vittorio; Castoldi, Laura; Mamuye, Ashenafi Damtew; Langer, Thierry; Holzer, Wolfgang
- Abstract
An efficient, chemoselective approach to spiro-epoxyoxindoles via the addition of chloromethyllithium followed by ring-closure of the intermediate alkoxide is reported. Chemoselectivity is fully preserved in the presence of different electrophilic sites. The synthetic potential of selected spiro-epoxyindoles has been exploited in the copper(I)-catalyzed intramolecular oxyarylation of an alkyne and in the formation of N,N-dimethylisoindigo via the addition of dihalocarbenoids.
- Subjects
CHEMOSELECTIVITY; ADDITION reactions; METHYLLITHIUM; ISATIN; INDOLE compounds; RING formation (Chemistry); ELECTROPHILES; ARYLATION
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 2, p172
- ISSN
1615-4150
- Publication type
Academic Journal
- DOI
10.1002/adsc.201500840