SYNTHESIS OF ENANTIOMERICALLY PURE 3-FLUOROMETHYLTHREONINES FROM (S)-1-FLUORO-3-TOLYLSULFINYLACETONE

Authors
ARNONE A GESTMANN D MEILLE SV RESNATI G SIDOTI G
Citation
A. Arnone et al., SYNTHESIS OF ENANTIOMERICALLY PURE 3-FLUOROMETHYLTHREONINES FROM (S)-1-FLUORO-3-TOLYLSULFINYLACETONE, Chemical communications, (22), 1996, pp. 2569-2570
Citations number
25
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
22
Year of publication
1996
Pages
2569 - 2570
Database
ISI
SICI code
1359-7345(1996):22<2569:SOEP3F>2.0.ZU;2-C
Abstract
The copper(I) catalysed aldol reaction between methyl isocyanoacetate and (S)-3-fluoro-1-(4-methylphenyl)-sulfinylacetone affords oxazoline products which, after diastereoisomer separation, give in high yields optically pure 3-fluoromethylthreonine analogues whose absolute and re lative configurations have been assigned through X-ray analyses.