Use of bis-(chiral alpha-methylbenzyl)glycine esters for synthesis of enantiopure beta-hydroxyamino esters.
[reaction: see text] Aldol reactions using bis-(chiral alpha-methylbenzyl)glycine esters with aldehydes gave excellent diastereoselectivity. Thus, an enantiopure ribosylglycine was prepared for the synthesis of analogues of the natural antibiotics muraymycin. This method was extended for formation of beta-hydroxyamino esters.
Yamashita
Ayako
A
Chemical Sciences, Wyeth Research, Pearl River, New York 10965, USA.
Norton
Emily B
EB
Williamson
R Thomas
RT
Ho
Douglas M
DM
Sinishtaj
Sandra
S
Mansour
Tarek S
TS
D000447:Aldehydes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis*; D005998:Glycine / Q000031:analogs & derivatives*; D006877:Hydroxamic Acids / Q000138:chemical synthesis*; D015394:Molecular Structure; D009711:Nucleotides; D010455:Peptides; D010457:Peptidoglycan / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D004952:Esters; D006877:Hydroxamic Acids; D009711:Nucleotides; D010455:Peptides; D010457:Peptidoglycan; C475706:muraymycin A1; D014508:Urea; D005998:Glycine