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Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes
Author(s) -
Kossler David,
Perrin Florian G.,
Suleymanov Abdusalom A.,
Kiefer Gregor,
Scopelliti Rosario,
Severin Kay,
Cramer Nicolai
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201706013
Subject(s) - enantioselective synthesis , chemistry , triazene , cycloaddition , combinatorial chemistry , halide , catalysis , organic chemistry , cyclopentadienyl complex
Abstract Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1‐alkynyl triazenes in the presence of a Ru II catalyst with a chiral cyclopentadienyl ligand. These triazenes serve as unique vinyl cation surrogates. Under acidic conditions, the triazene functionality can be replaced with a variety of groups, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a pool of chiral polycyclic compounds.