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

Fatih Sirindil | Zendy; Stéphane Golling | Zendy; Raphaël Lamare | Zendy; JeanMarc Weibel | Zendy; Patrick Pale | Zendy; Aurélien Blanc | Zendy

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

Author(s) -

Fatih Sirindil,

Stéphane Golling,

Raphaël Lamare,

JeanMarc Weibel,

Patrick Pale,

Aurélien Blanc

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03402

Subject(s) - azepine , chemistry , cycloisomerization , indolizine , sulfonyl , dichloromethane , catalysis , cascade , medicinal chemistry , combinatorial chemistry , cascade reaction , azulene , bicyclic molecule , domino , biphenyl , stereochemistry , organic chemistry , solvent , alkyl , chromatography

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- er -butylphosphine]gold(I) triflimide complex in dichloromethane.

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