The[3+2]cycloaddition reaction of α,β-epoxy carboxylate and isocyanate was investigated.By employing magnesium bromide as a catalyst,efficient synthesis of chiral oxazolidin-2-ones was achieved through aforementioned[3+2]cycloaddition reaction.The reaction exhibited good substrate adaptability.For reactions involving chiral epoxide compounds,the product enantiomeric excess remains good.Furthermore,under basic conditions,taxol C-13 side chain((2R,3S)-methyl 3-benzamido-2-hydroxy-3-phenylpropanoate)was synthesized via ring-opening reaction of the chiral oxazolidin-2-ones product with an optical purity of up to 97%ee.
asymmetric synthesis[3+2]cycloadditionoxazolidin-2-onetaxol side chain