Abstract
β-Amino-α-fluoro esters have been prepared stereoselectively from t-butyl cinnamate and ethyl crotonate via tandem conjugate addition of lithium (S)-(-)-N-benzyl-N-α-methylbenzylamide, followed by fluorination with N-fluorobenzenesulfonimide. The absolute stereochemistry of the major diastereomers formed in each reaction was confirmed by X-ray crystallography. Complete deprotection to give (2S,3S)-α-fluoro-β-phenylalanine followed by Fmoc protection was achieved.
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