Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation.
A series of protected beta2-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained (up to 91%) with full conversion for a number of beta-amino acids.
Hoen
Rob
R
Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Tiemersma-Wegman
Theodora
T
Procuranti
Barbara
B
Lefort
Laurent
L
de Vries
Johannes G
JG
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
D000438:Alcohols / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D006859:Hydrogen / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000438:Alcohols; D000596:Amino Acids; D008024:Ligands; D010455:Peptides; D006859:Hydrogen; D012238:Rhodium