Synthesis of homoserine samples stereospecifically labelled with isotopic hydrogen in the β- and γ-positions

Abstract

(βR)[β-²H]-L-Homoserine (17) and the (βS)-isomer (8) are synthesised through a sequence involving as key step the formal cis addition of hydroxylamine onto cinnamic acid to form 3-amino-3-phenylpropionic acid; (γR)[γ-²H]-DL-homoserine (20) and the (γS)-isomer (19) are obtained from the enantiomeric forms of stereospecifically labelled 3-phenyl[1-²H]propanol.