Asymmetric enamide hydrogenation using phosphinite thioglycosides: synthesis of D- and L-aminoesters using D-sugars as catalyst precursors.
Diastereomerically pure cationic Rh(I) complexes derived from phosphinite thioglycosides I were used as catalysts in highly enantioselective hydrogenations of enamides. The conformational similarity of alpha-D-arabinopyranose with beta-L-galactopyranose allows the synthesis of both enantiomers of alpha-amino acid derivatives such as D- and L-DOPA in excellent ee (97% and 98%), using derivatives of the former sugar as catalyst precursors.
Khiar
Noureddine
N
Instituto de Investigaciones Químicas, C.S.I.C-Universidad de Sevilla, c/. Américo Vespucio, 49, Isla de la Cartuja, 41092 Sevilla, Spain. khiar@iiq.csic.esinmaff@us.es
Navas
Raquel
R
Suárez
Belén
B
Alvarez
Eleuterio
E
Fernández
Inmaculada
I
D000475:Alkenes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis; D001089:Arabinose / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D004295:Dihydroxyphenylalanine / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis; D005690:Galactose / Q000737:chemistry; D006865:Hydrogenation; D010721:Phosphinic Acids / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
D000475:Alkenes; D000577:Amides; D000588:Amines; D002241:Carbohydrates; D004952:Esters; D010721:Phosphinic Acids; D013865:Thioglycosides; D004295:Dihydroxyphenylalanine; D001089:Arabinose; D012238:Rhodium; D005690:Galactose