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Synfacts 2005(2): 0208-0208
DOI: 10.1055/s-2005-916060
DOI: 10.1055/s-2005-916060
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Intramolecular Hydroamination Route to Thiazolidine-1,1-dioxides
T. P. Zabawa, D. Kasi, S. R. Chemler*
State University of New York, USA
Further Information
Publication History
Publication Date:
25 October 2005 (online)
Significance
An intramolecular double amination route to 1,2-diamines from readily available alkyl- and aryl-substituted N-benzylsulfamides via thiadiazolidine-1,2-dioxides is reported. The reaction involves an intramolecular hydroamination-NH insertion path of an unactivated double bond under Cu catalysis. It has limited scope (R = H and Me) and proceeds for thiadiazolidine fused with pyrrolidines, isoindolidines, tetrahydroquinolines, and tetrahydroisoquinolines in moderate to good yields.