ENRICHMENT, CHARACTERIZATION AND ABSOLUTE-CONFIGURATION OF THE ENANTIOMERS OF 1-(3,5-DIMETHOXYPHENYL)-2-(4-METHOXYPHENYL)ETHANOL

Authors
TALVITIE A MANNILA E KRAL A
Citation
A. Talvitie et al., ENRICHMENT, CHARACTERIZATION AND ABSOLUTE-CONFIGURATION OF THE ENANTIOMERS OF 1-(3,5-DIMETHOXYPHENYL)-2-(4-METHOXYPHENYL)ETHANOL, Acta chemica Scandinavica, 50(12), 1996, pp. 1143-1146
Citations number
14
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
50
Issue
12
Year of publication
1996
Pages
1143 - 1146
Database
ISI
SICI code
0904-213X(1996)50:12<1143:ECAAOT>2.0.ZU;2-B
Abstract
The racemate and enriched enantiomers of 1-(3,5-dimethoxyphenyl)-2-(4- methoxyphenyl) ethanol have been obtained via reduction of the respect ive ketone with LiAlH4 and with BH3 in the presence of oxazaborolidine s. Enriched enantiomers were characterized by H-1 NMR spectroscopy, to gether with the Eu-d-(hfbc)(3) reagent, and by polarimetry. The absolu te configuration was obtained by H-1 and C-13 NMR spectroscopy from th e (S)-MTPA esters. The configuration of the esters was optimized by fo rce-held calculation.