The Lindlar Catalyst Revitalized: A Highly Chemoselective Method for the Direct Conversion of Azides to N-(tert-Butoxycarbonyl)amines
P. Ganapati Reddy, T. V. Pratap, Govindharaj Kumar, Subhendu K. Mohanty, Sundarababu Baskaran · European Journal of Organic Chemistry · 2002
An exceptionally chemoselective method for the direct conversion of azides to N-(tert-butoxycarbonyl)-protected amines under catalytic transfer-hydrogenation conditions, using the Lindlar catalyst, is reported. The extremely labile functional groups such as N-Cbz, benzyl ester are shown to be inert under the reaction conditions. The present method allows us to synthesize orthogonally protected (N-Cbz & N-Boc) 1,2-diamino systems, which will be immensely useful in organic synthesis. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)