Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes. Issue 38 (9th August 2017)

• Record Type: Journal Article
• Authors: Kossler, David; Perrin, Florian G.; Suleymanov, Abdusalom A.; Kiefer, Gregor; Scopelliti, Rosario; Severin, Kay; Cramer, Nicolai
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 38(2017)
• Page Start: 11490
• Page End: 11493
• Publication Date: 2017-08-09
• Subjects: asymmetric catalysis -- cycloaddition -- divergent synthesis -- ruthenium -- triazenes; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201706013
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : In with the new, in with the Nu : 1‐Alkynyl triazenes and bicyclic alkenes underwent enantioselective [2+2] cycloaddition catalyzed by a chiral cyclopentadienyl Ru II complex to give vinyl triazenes. The triazene functionality was readily replaced with a variety of nucleophiles, including halides, alkoxides, sulfoxides, amides, arenes, and heteroarenes, thus providing efficient access to a wide range of chiral polycyclic compounds.