A short route to (±)-N-hydroxylysine and (±)-laminine by palladium-catalyzed reactions

Article abstract of DOI:10.1055/s-1993-25858

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-butoxycarbonyl-oxy)carbamate, dimethylamine and methyl (diphenylmethyleneamino) acetate. Hydrogenation and hydrolysis of the 1,4-adducts afforded N⁶-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.