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Updated: Aug 21, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Rh(II)-catalyzed Doyle-Kirmse reaction: access to unprotected 3-allyl/3-allenyl-3-(thio)oxindoles
Xunbo Lu1, Kaiyuan Yang1, Xinyu Xu1
1School of Chemistry and Chemical Engineering, Laboratory of Marine Green Fine Chemicals, Lingnan Normal University, Zhanjiang, 524048, P. R. China. luxunbo@foxmail.com.
Abstract:
The construction of the 3-allyl/3-allenyl-3-(thio)oxindole core remains a challenge in organic synthesis. Herein, we report a novel Rh2(esp)2 catalytic Doyle-Kirmse reaction to furnish the oxindole core, bearing unbiased NH as well as a quaternary stereogenic center at the 3-position, in good to excellent yields under mild conditions. These reactions are concise, practical, atom-economic, and highly efficient, and feature a TON of up to 3700. Moreover, a non-radical pathway was observed in this approach.
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