Construction of quaternary carbon centers by using substitution of γ,γ-disubstituted secondary allylic picolinates with alkylcopper reagents
Construction of quaternary carbon centers by using substitution of γ,γ-disubstituted secondary allylic picolinates with alkylcopper reagents
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DOI：
10.1016/j.tetlet.2013.06.046
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发表时间：
2013-08-28
影响因子：
1.8
通讯作者：
Kobayashi, Yuichi
中科院分区：
文献类型：
--
作者：
Feng, Chao;Kaneko, Yuki;Kobayashi, Yuichi
ZnI 2被发现促进区域和立体选择性取代的γ，γ-二取代的仲烯丙基吡啶甲酸酯与烷基铜试剂衍生自烷基-MgBr和CuBr中心点Me 2S在2：1的比例，以提供良好的产率季碳中心。有效递送的烷基是伯、仲和苄基类，例如Me、Et、Bu、C16 H33、Ph（CH 2）（2）、Ph（CH 2）（3）、c-C6 H11和Bn。作为一个应用，烯丙基吡啶甲酸酯与（E）-或（Z）-烯烃提供季碳中心，它们是彼此的对映异构体。(C)2013爱思唯尔有限公司保留所有权利。
ZnI2 was found to promote regio- and stereoselective substitution of gamma,gamma-disubstituted secondary allylic picolinates with alkylcopper reagents derived from alkyl-MgBr and CuBr center dot Me2S in a 2:1 ratio to furnish quaternary carbon centers in good yields. Alkyl groups delivered efficiently were the primary, secondary, and benzyl classes such as Me, Et, Bu, C16H33, Ph(CH2)(2), Ph(CH2)(3), c-C6H11, and Bn. As an application, allylic picolinates with the (E)- or (Z)-olefin afforded quaternary carbon centers that are the enantiomers of each other. (C) 2013 Elsevier Ltd. All rights reserved.