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Reaction of Vinyl Aziridines with Arynes: Synthesis of Benzazepines and Branched Allyl Fluorides
Author(s) -
Kaldas Sherif J.,
Kran Eva,
MückLichtenfeld Christian,
Yudin Andrei K.,
Studer Armido
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904727
Subject(s) - benzazepines , aryne , allylic rearrangement , chemistry , cycloaddition , enantiopure drug , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis
We report the cycloaddition between vinyl aziridines and arynes. Depending on the reaction conditions and the choice of the aryne precursor, the aziridinium intermediate can be trapped through two distinct mechanistic pathways. The first one proceeds through a formal [5+2] cycloaddition to furnish valuable multi‐substituted benzazepines. In the second pathway, the aziridinium is intercepted by a fluoride ion to afford allylic fluorides in good yields. Both reactions proceed stereospecifically and furnish enantiopure benzazepines and allylic fluorides.