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The Lindlar catalyst revitalized: A highly chemoselective method for the direct conversion of azides to N-(tert-butoxycarbonyl)amines
Date Issued
01-11-2002
Author(s)
Ganapati Reddy, P.
Verabhadra Pratap, T.
Kishore Kumar, G. D.
Mohanty, Subhendu K.
Indian Institute of Technology, Madras
Abstract
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.