Diastereoselective reduction of a chiral N-Boc-protected delta-amino-alpha,beta-unsaturated gamma-keto ester Phe-Gly dipeptidomimetic.
The readily available N-Boc-protected delta-amino alpha,beta-unsaturated gamma-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)(3) in EtOH at -78 degrees C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 degrees C under Felkin-Anh control.
Våbenø
Jon
J
Department of Medicinal Chemistry, Institute of Pharmacy, University of Tromsø, N-9037 Tromsø, Norway.
Brisander
Magnus
M
Lejon
Tore
T
Luthman
Kristina
K
D000535:Aluminum / Q000737:chemistry; D000605:Amino Alcohols / Q000032:analysis / Q000138:chemical synthesis*; D001895:Boron / Q000737:chemistry; D002208:Caproates / Q000737:chemistry*; D002614:Chelating Agents; D004151:Dipeptides / Q000737:chemistry*; D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D019163:Reducing Agents; D013237:Stereoisomerism
D000605:Amino Alcohols; D002208:Caproates; D002614:Chelating Agents; D004151:Dipeptides; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D019163:Reducing Agents; C474141:tert-butyl (5S)-5-(N-(tert-butoxycarbonyl)amino)-4-oxo-6-phenyl-(E)-2-hexenoate; C040500:phenylalanylglycine; D008094:Lithium; D000535:Aluminum; D001895:Boron