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Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N-tosylhydrazones under metal-free conditions |
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| Authors: | Xufeng Nie Yachuan Wang Lijun Yang Zaijun Yang Tairan Kang |
| Affiliation: | 1. Chemical Synthesis and Pollution Control Key Laboratory/Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, 1 Shida Road, Nanchong 637000, China;2. State Key Laboratory of Biotherapy/Collaborative Innovation Center of Biotherapy, Cancer Center, West China Hospital, 3 People''s South Road, Chengdu 610000, China |
| Abstract: | A metal-free cyclopropanation of electron-deficient olefins 3-substituted-2-cyanoacrylamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides with a quaternary stereogenic center in good yields and with high diastereoselectivities (up to 90% yield with 19:1 dr). The reaction could be performed in one-pot fashion and in a gram-scale from aryl aldehydes. |
| Keywords: | 1-Cyanocyclopropane carboxamides Electron-deficient olefins Transition-metal-free Diazomethane |
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