Picolinoxy group, a new leaving group for anti SN2′ selective allylic substitution with aryl anions based on Grignard reagents
Picolinoxy group, a new leaving group for anti SN2′ selective allylic substitution with aryl anions based on Grignard reagents
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DOI：
10.1021/ol800300x
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发表时间：
2008-05-01
期刊：
影响因子：
5.2
通讯作者：
Kobayashi, Yuichi
中科院分区：
文献类型：
--
作者：
Kiyotsuka, Yohei;Acharya, Hukum P.;Kobayashi, Yuichi
研究发现，吡咯烷氧基是芳基亲核试剂取代烯丙基的一个非常有效的离开基团。取代以反S(N)2‘途径进行，具有较高的手性转移。成功的原因可能是吡啶基团的电子吸引效应和对镁溴的络合作用。结果表明，这些效应是存在的。
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 S(N)2' 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.