%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