Abstract
The reaction of chiral α-hydroxy β,γ-unsaturated esters with tosyl isocyanate followed by cyclization of the resulting allylic carbamates with iodine in the presence of sodium carbonate provided trans-4,5-disubstituted 2-oxazolidinone derivatives in a highly diastereoselective manner. The subsequent removal of the iodo group and the protective functionality afforded the syn- β-amino-α-hydroxy acids. Using the reaction sequence, (2 R,3 S)- and (2 S,3 R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity.
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