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Synthesis 1993; 1993(3): 321-324
DOI: 10.1055/s-1993-25858
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A Short Route to (±)-N-Hydroxylysine and (±)-Laminine by Palladium-Catalyzed Reactions

Jean Pierre Genet* , Serge Thorimbert, Sergio Mallart, Nathalie Kardos
  • *Laboratoire de Synthèse organique, associé au CNRS; Ecole Nationale Supérieure de Chimie de Paris, 11 Rue Pierre et Marie Curie, F-75231 Paris, France
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Publikationsdatum:
17. September 2002 (online)

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The title compounds were conveniently synthesized by efficient sequential one-pot amination-alkylation starting from (Z)-4-acetoxy-2-butenyl ethyl carbonate (3) with tert-butyl (tert-butoxycarbonyloxy)carbamate, dimethylamine and methyl (diphenylmethyleneamino) acetate. Hydrogenation and hydrolysis of the 1,4-adducts afforded N 6-hydroxylysine [2-amino-6-(hydroxyamino)hexanoic acid, 1) and laminine hydrochloride [2-amino-6-(trimethylammonio)hexanoic acid chloride, 2] in 65 % and 39 % yield, respectively.