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

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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… Click to show full abstract

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.

Keywords: pyrrolo azepine; azepine derivatives; azepine; gold; synthesis indolizine; indolizine pyrrolo

Journal Title: Organic letters
Year Published: 2019

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