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. 2008 May 1;10(9):1719-22.
doi: 10.1021/ol800300x. Epub 2008 Apr 9.

Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents

Yohei Kiyotsuka  1 , Hukum P Acharya, Yuji Katayama, Tomonori Hyodo, Yuichi Kobayashi
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Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents

Yohei Kiyotsuka et al. Org Lett. .

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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