A Short Route to (±)-N-Hydroxylysine and (±)-Laminine by Palladium-Catalyzed Reactions

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.