Abstract
An efficient, stereoselective synthetic strategy to d- threo-3-hydroxyaspartic acid was developed. Starting from l-(2 S,3 S)- N-benzoyl-3-hydroxyaspartic acid dimethyl ester by a Deoxo-fluor-catalyzed cyclization reaction, an inversion of configuration at the β-center ( erythro isomer), was observed. A base-induced epimerization reaction led to the d- trans-isomer, which was hydrolyzed to give d- threo-3-hydroxyaspartic acid with excellent stereoselectivity and overall yield. Starting from d- threo-3-hydroxyaspartic acid, l- threo-oxazolines can be stereoselectively synthesized.
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