Asymmetric synthesis of polyhydroxy alpha-amino acids with the sulfinimine-mediated asymmetric strecker reaction: 2-amino 2-deoxy L-xylono-1,5-lactone (polyoxamic acid lactone).
Polyhydroxylated sulfinimines derived from protected 1,2-O-isopropyliden-L-threoses undergo the sulfinimine-mediated Strecker syntheses to give alpha-amino nitriles in good yield and de. A double stereodifferentiation effect was not observed and the diastereoselectivity is controlled by the absolute configuration of the sulfinyl group. Hydrolysis of the amino nitriles afforded the lactone rather than polyoxamic acid.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122-2585, USA. fdavis@astro.ocis.temple.edu
Prasad
Kavirayani R
KR
Carroll
Patrick J
PJ
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D001383:Azetidinecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D007783:Lactones; D009570:Nitriles; C010624:polyoximic acid; D001383:Azetidinecarboxylic Acid