John I. Trujillo

Convenient Access to Sulfinyl Derivatives of Heterocycles

Significance: Sulfinyl derivatives are compounds with important biological properties (e.g., esomeprazole and modafinil) or chemical properties (see Book below). The use of tert-butylsulfinamide for the enantioselective synthesis of amines is well documented (M. T. Robak, M. A. Herbage, J. A. Ellman Chem. Rev. 2010,110, 3600). Also, an optically active sulfinamide has been used as a cocatalyst in the asymmetric protonation of enol silanes (E. M. Beck, A. M. Hyde, E. N. Jacobsen Org. Lett. 2011, 13, 4260). Finally, a sulfinamide may be considered to be isosteric to a carboxamide with the additional feature of chirality.