GENERAL-APPROACH TO HYDROXYLATED ALPHA-AMINO-ACIDS EXPLOITING UTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE

Authors
RASSU G ZANARDI F CORNIA M CASIRAGHI G
Citation
G. Rassu et al., GENERAL-APPROACH TO HYDROXYLATED ALPHA-AMINO-ACIDS EXPLOITING UTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE, Journal of the Chemical Society. Perkin transactions. I, (17), 1994, pp. 2431-2437
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
17
Year of publication
1994
Pages
2431 - 2437
Database
ISI
SICI code
0300-922X(1994):17<2431:GTHAEU>2.0.ZU;2-B
Abstract
Racemic beta-hydroxy-alpha-amino acids 7a, 7b and 10 of either three o r erythro configuration have been efficiently synthesized from simple aldehydes, utilizing tert-butoxycarbonyl)-2-(tert-butyl-dimethylsiloxy ) pyrrole (TBDMSOP) as a glycine-anion equivalent. Similar methodology , employing readily available aldehydo sugar precursors, has been succ essfully applied to syntheses of enantiomerically pure polyhydroxylate d alpha-amino acids 14a-14f possessing diverse constitution and chiral ity.