Synthesis of enantiomerically pure 3-fluoromethylthreonines from (S)-1-fluoro-3-tolylsulfinylacetone
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 relative configurations have been assigned through X-ray analyses.