Synthesis of (+)-(R)-methyl 2-aminotetraline-2-carboxylate: the hydroxypinanone method versus the bislactim method

The methyl ester of 2-aminotetraline-2-carboxylic acid (Atc-OMe), an import ant residue for modified peptides, could only be synthesized From the Schol lkopf bislactim method. the hydroxypinanone method leading, during the seco nd step, to elimination instead of alkyation toward the expected spiro prod uct. The (+)-(R)-Atc-OMe was thus obtained in three steps and 55% overall y ield From the (-)-(R)-bislactim derived from D-valine. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.