Spirooxindoles containing nitrogen heterocycles display a wide variety of biological activity. We have recently developed a Lewis acid catalyzed method for allylsilane annulation with N-Boc-iminooxindoles to access silicon-containing spirocarbamates. Several Lewis acids (e.g. Cu(II), Sc(III), and Y(III) salts) effectively catalyze this reaction with sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBArF) as a critical additive to obtain the desired spirocarbamate product in high yields. The spirocarbamates can be further derivatized to obtain furoindolines upon reduction or 3- amino-3-allyl oxindoles through a fluoride-promoted elimination of the silicon group. Biological activity of these spirooxindoles and their derivatives will also be presented.

Lewis acid catalyzed synthesis of spirocarbamate oxindoles and derivatives

248th National Meeting (2014)

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