Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles
Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles
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DOI：
10.1021/acs.orglett.5b00571
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发表时间：
2015-04-17
期刊：
影响因子：
5.2
通讯作者：
Zhu, Jieping
中科院分区：
文献类型：
--
作者：
Bunescu, Ala;Wang, Qian;Zhu, Jieping
以未活化的烷基腈为反应对体，研究了铜催化烯丙醇的烷氧基化反应。提出了一个涉及生成烷基腈自由基，然后将其添加到双键和铜介导的C（sp（3））-O键的形成的序列来解释反应结果。该方案提供了一个有效的路线，通过形成一个C（sp（3））C（sp（3））和C（sp（3））-O键的功能化的三-和四取代的环氧化物具有中等至优异的非对映选择性。
A copper-catalyzed oxyalkylation of allylic alcohols using nonactivated alkyl nitriles as reaction partners was developed. A sequence involving generation of an alkyl nitrile radical followed by its addition to a double bond and a copper-mediated formation of C(sp(3))-O bond was proposed to account for the reaction outcome. The protocol provided an efficient route to functionalized tri- and tetrasubstituted epoxides via formation of a C(sp(3))C(sp(3)) and a C(sp(3))-O bond with moderate to excellent diastereoselectivity.