185015-84-3Relevant academic research and scientific papers
Enantiospecific and diastereoselective synthesis of syn-β-amino-α-hydroxy acids
Sugimura, Hideyuki,Miura, Masayuki,Yamada, Nobuko
, p. 4089 - 4099 (1997)
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, (2R,3S)- and (2S,3R)-3-amino-2-hydroxy acids were synthesized with high enantioselectivity.
