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

Acylcyclopropanes are employed as useful donor–acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole an...

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Bibliographic Details
Published in:Organic letters 2021-03, Vol.23 (6), p.2326-2331
Main Authors: Ortega, Alesandere, Uria, Uxue, Tejero, Tomás, Prieto, Liher, Reyes, Efraim, Merino, Pedro, Vicario, Jose L.
Format: Article
Language:English
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Letter
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Summary:Acylcyclopropanes are employed as useful donor–acceptor cyclopropanes that undergo formal (4 + 2) cyclocondensation with N-unprotected 3-substituted indoles in the presence of a Brønsted acid catalyst. The reaction involves the simultaneous alkylation of both the N and C-2 positions of the indole and provides access to the 8,9-dihydro­pyrido­[1,2-a]­indole scaffold that is the central core of several biologically relevant indole alkaloids in excellent yields and good selectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00470