Enantioselective dearomative [3 + 2] cycloaddition reaction of 2-nitrobenzofurans with 3-isothiocyanato oxindoles was developed. The reaction employs a chiral bis(oxazoline)/Zn(OTf)2 catalyst, allowing a practical, straightforward access to structurally diverse spirooxindoles… Click to show full abstract
Enantioselective dearomative [3 + 2] cycloaddition reaction of 2-nitrobenzofurans with 3-isothiocyanato oxindoles was developed. The reaction employs a chiral bis(oxazoline)/Zn(OTf)2 catalyst, allowing a practical, straightforward access to structurally diverse spirooxindoles containing a 2,3-dihydrobenzofuran motif and three contiguous stereocenters with excellent diastereo- and enantioselectivities. The synthetic potentials of the method have been demonstrated by the scale-up experiment and transformations of the products. The preliminary mechanism was investigated with experimental observations, nonlinear effects studies, and MS experiments.
               
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