Synthesis of Indolizine and Pyrrolo[1,2‑a]azepine Derivatives via a Gold(I)-Catalyzed Three-Step Cascade

Synthesis of Indolizine and Pyrrolo[1,2‑a]azepine Derivatives via a Gold(I)-Catalyzed Three-Step Cascade

Linear N-alkenyl or alkynyl N-sulfonyl 1-aminobut-3-yn-2-ones are converted into bicyclic indolizines and pyrrolo­[1,2-a]­azepine-type alkaloids upon gold­(I) catalysis (17 examples, 10–85%). The reaction cascade allowed formation of C–N, O–S, and C–C bonds via a cycloisomerization/sulfonyl migratio...

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Veröffentlicht in:Organic letters 2019-11, Vol.21 (22), p.8997-9000
Hauptverfasser: Sirindil, Fatih, Golling, Stéphane, Lamare, Raphaël, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien
Format: Artikel
Sprache:eng
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Chemical Sciences
Organic chemistry
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Zusammenfassung:Linear N-alkenyl or alkynyl N-sulfonyl 1-aminobut-3-yn-2-ones are converted into bicyclic indolizines and pyrrolo­[1,2-a]­azepine-type alkaloids upon gold­(I) catalysis (17 examples, 10–85%). The reaction cascade allowed formation of C–N, O–S, and C–C bonds via a cycloisomerization/sulfonyl migration/cyclization process using 10 mol % of [(2-biphenyl)­di-tert-butyl­phosphine]­gold­(I) triflimide complex in dichloromethane.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03402