jo982034j_si_001.pdf (102.13 kB)
Enantioselective Synthesis of Diamino Dicarboxylic Acids
journal contribution
posted on 1999-03-03, 00:00 authored by Johann Hiebl, Hermann Kollmann, Franz Rovenszky, Karin WinklerThe 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.