A simple route to complexity: An organocatalytic 1,3-dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1-hydroxy-1H-benzotriazole, MTBE=methyl tert-butyl ether, PG=protecting group, TMS=trimethylsilyl.
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Sun et al. (2013) studied this question.
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