Citation: Mei-Hua Shen, Chen Li, Qing-Song Xu, Bin Guo, Rui Wang, Xiaoqian Liu, Hua-Dong Xu, Defeng Xu. Allylation and alkylation of oxindoleketimines via imine umpolung strategy[J]. Chinese Chemical Letters, ;2021, 32(7): 2313-2316. doi: 10.1016/j.cclet.2021.02.026 shu

Allylation and alkylation of oxindoleketimines via imine umpolung strategy

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou 213164, China

shenmh@cczu.edu.cn

markxu@cczu.edu.cn

Received Date: 1 December 2020
Revised Date: 3 February 2021
Accepted Date: 10 February 2021
Available Online: 16 February 2021

Figures(6)

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.
- Allylation,
- Alkylation,
- Azaallylaion,
- Umpolung,
- Oxindleketamine,
- Spiro oxindole
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