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

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro-Epoxyoxindoles.

Pace, Vittorio; Castoldi, Laura; Mamuye, Ashenafi Damtew; Langer, Thierry; Holzer, Wolfgang