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.

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro-Epoxyoxindoles / V. Pace, L. Castoldi, A.D. Mamuye, T. Langer, W. Holzer. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 358:2(2016 Jan 05), pp. 172-177. [10.1002/adsc.201500840]

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

L. Castoldi
Secondo
;
2016

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.
carbenoids; chemoselectivity; epoxidation; Grignard reaction; homologation
Settore CHIM/06 - Chimica Organica
5-gen-2016
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890710
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