Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents |
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| Authors: | Kiyotsuka Yohei Acharya Hukum P Katayama Yuji Hyodo Tomonori Kobayashi Yuichi |
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| Affiliation: | Department of Biomolecular Engineering, Tokyo Institute of Technology, Yokohama, Japan. |
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| Abstract: | ![]()
The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr*Me2S. The substitution proceeds with anti SN2' pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained. |
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