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Ruthenium Pybox-Catalyzed Enantioselective Intramolecular C-H Amination of Sulfamoyl Azides en Route to Chiral Vicinal Diamines

Xin Nie, Zihan Yan, Sergei Ivlev and Eric Meggers*

*Fachbereich Chemie, Philipps-Universitšt Marburg, Hans-Meerwein-Strasse 4, 35043 Marburg, Germany, Email: meggerschemie.uni-marburg.de

X. Nie, Z. Yan, S. Ivlev, E. Meggers, J. Org. Chem., 2021, 86, 750-761.

DOI: 10.1021/acs.joc.0c02279 (free Supporting Information)


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Abstract

A catalytic asymmetric ring-closing 1,5-C-H amination of sulfamoyl azides provides chiral 1,2,5-thiadiazolidine-1,1-dioxides in up to 98% yield and up to 98% ee if the C-H bond is in a benzylic position. The reaction is catalyzed by a recently introduced simple chiral ruthenium bis(oxazoline) (pybox) complex.


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Key Words

N-heterocycles, S-heterocycles, 1,2-diamines


ID: J42-Y2021