ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF -ALPHA-BROMO-ALPHA-FLUORO-BETA-HYDROXYCARBOXYLATES

Authors
ISEKI K KUROKI Y KOBAYASHI Y
Citation
K. Iseki et al., ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF -ALPHA-BROMO-ALPHA-FLUORO-BETA-HYDROXYCARBOXYLATES, Synlett, (4), 1998, pp. 437
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
4
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):4<437:EADSO->2.0.ZU;2-5
Abstract
Reaction of aldehydes with bromofluoroketene silyl acetal 1 in the pre sence of 20 mol% chiral Lewis acid 2 proceeds with enantio- and diaste reoselectivities at -20 degrees C to afford optically active anti-alph a-bromo-alpha-fluoro-beta-hydroxy esters 3a-f (up to 89:11 anti:syn, u p to 93% ee).