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. 2017 Sep 11;56(38):11490-11493.
doi: 10.1002/anie.201706013. Epub 2017 Aug 9.

Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes

David Kossler  1 , Florian G Perrin  1 , Abdusalom A Suleymanov  1 , Gregor Kiefer  1 , Rosario Scopelliti  1 , Kay Severin  1 , Nicolai Cramer  1
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Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes

David Kossler et al. Angew Chem Int Ed Engl. .

Abstract

Vinyl triazenes were obtained by enantioselective [2+2] cycloaddition reactions of bicyclic alkenes with 1-alkynyl triazenes in the presence of a RuII 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.

Keywords: asymmetric catalysis; cycloaddition; divergent synthesis; ruthenium; triazenes.

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