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Efficient Trapping of 1,2‐Cyclohexadienes with 1,3‐Dipoles
Author(s) -
Lofstrand Verner A.,
West Frederick G.
Publication year - 2016
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.201602201
Subject(s) - chemistry , nucleophile , allene , trapping , azide , intermolecular force , combinatorial chemistry , functional group , dipole , photochemistry , medicinal chemistry , organic chemistry , catalysis , molecule , ecology , biology , polymer
1,2‐Cyclohexadienes are transient intermediates that undergo rapid dimerization and intermolecular trapping with activated olefins and heteroatomic nucleophiles. Fluoride‐mediated desilylative elimination of readily accessible 6‐silylcyclohexene‐1‐triflates allows the mild, chemoselective, and functional‐group tolerant generation of cyclic allene intermediates, which undergo efficient trapping reactions with stable 1,3‐dipoles. The reactions proceed with high levels of both regio‐ and diastereoselectivity. The reaction of cyclic allenes with azides is accompanied by the facile loss of dinitrogen, resulting in the formation of tetrahydroindoles or polycylic aziridines depending on the azide employed.