Allylation and alkylation of oxindoleketimines via imine umpolung strategy |
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| Authors: | Mei-Hua Shen Chen Li Qing-Song Xu Bin Guo Rui Wang Xiaoqian Liu Hua-Dong Xu Defeng Xu |
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| Affiliation: | Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou 213164, China |
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| Abstract: | When treated with an alkoxide base like t-BuOK in aprotic solvent, N-diphenylmethyl imino oxindoles, made conveniently through condensation of corresponding isatins with N-diphenylmethyl amine, are deprotonated to form azaallyl anions. Allylation and alkylation of this type of intermediates proceed smoothly with diverse C-electrophiles. Acidic work up finishes 3-amino-3-allyl/alkyl oxindoles. The overall transformation equals to an umpolung process at the C3 of isatins. |
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| Keywords: | Allylation Alkylation Azaallylaion Umpolung Oxindleketamine Spiro oxindole |
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