THE ENANTIOSELECTIVE SYNTHESIS OF ANTI-BETA-HYDROXY-ALPHA-AMINO ACIDSVIA THE REACTION OF LITHIUM ENOLATES OF GLYCINE BEARING AN OXAZOLIDINE CHIRAL AUXILIARY WITH ALDEHYDES

Authors
IWANOWICZ EJ BLOMGREN P CHENG PTW SMITH K LAU WF PAN YY GU HH MALLEY MF GOUGOUTAS JZ
Citation
Ej. Iwanowicz et al., THE ENANTIOSELECTIVE SYNTHESIS OF ANTI-BETA-HYDROXY-ALPHA-AMINO ACIDSVIA THE REACTION OF LITHIUM ENOLATES OF GLYCINE BEARING AN OXAZOLIDINE CHIRAL AUXILIARY WITH ALDEHYDES, Synlett, (6), 1998, pp. 664
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
6
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):6<664:TESOAA>2.0.ZU;2-K
Abstract
A new anti-selective aldol reaction utilizing 2,4-disubstituted oxazol idine functionalized-glycine ester 1 is described. The corresponding l ithium enolate of 1, has been demonstrated to undergo a highly anti-di astereoselective aldol reation with a variety of aldehydes. Facile rem oval of the chiral auxiliary allows for the efficient preparation of c hiral beta-hydroxy-alpha-amino acids of erythro stereochemistry.