Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor–Acceptor Cyclopropanes

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2021-03
Autor
Ortega, Alesandere
Uria Pujana, Uxue ORCID
Tejero, Tomás
Prieto Aretxabaleta, Liher ORCID
Reyes Martín, Efraim
Merino, Pedro
Vicario Hernando, José Luis ORCID
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Organic Letters 23(6) : 2326-2331 (2021)
URI
http://hdl.handle.net/10810/69960
Resumen
Acylcyclopropanes are employed as useful donor−acceptor cyclopropanes that undergo formal (4 + 2) cyclo-condensation with N-unprotected 3-substituted indoles in thepresence of a Brønsted acid catalyst. The reaction involves thesimultaneous alkylation of both the N and C-2 positions of theindole and provides access to the 8,9-dihydropyrido[1,2-a]indolescaffold that is the central core of several biologically relevantindole alkaloids in excellent yields and good selectivities
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