%0 Journal Article %A Hiebl, Johann %A Kollmann, Hermann %A Rovenszky, Franz %A Winkler, Karin %D 1999 %T Enantioselective Synthesis of Diamino Dicarboxylic Acids %U https://acs.figshare.com/articles/journal_contribution/Enantioselective_Synthesis_of_Diamino_Dicarboxylic_Acids/3716499 %R 10.1021/jo982034j.s001 %2 https://acs.figshare.com/ndownloader/files/5808063 %K hydrogenation %K DAS %K alkyl diamino dicarboxylic acids %K prochiral precursors %K Diamino Dicarboxylic Acids %K succinic dialdehyde %K diunsaturated precursors %K DAA %K DAZ %K Enantioselective Synthesis %K Aqueous solutions %X The preparation of alkyl diamino dicarboxylic acids with high optical purity (100% ee, >98.5% de) and high yields based on asymmetric catalytic hydrogenation is described. The required prochiral precursors are prepared from dialdehydes and Z-, Boc-, and acetyl-protected phosphonoglycines. Aqueous solutions of glyoxal, succinic dialdehyde, and glutaric dialdehyde were used to prepare the diunsaturated precursors for 2,5-diaminoadipic acid (DAA), 2,7-diaminosuberic acid (DAS), and 2,8-diaminoazelaic acid (DAZ). Z-Protected dimethyl esters of DAA, DAS, and DAZ were obtained by hydrogenation of the corresponding prochiral starting materials with [(COD)Rh(S,S)-Et-DuPHOS]OTf. %I ACS Publications