Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes
Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Triazoles with Internal Alkynes and Terminal Allenes
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DOI：
10.1021/acs.orglett.7b03708
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发表时间：
2018-02-02
期刊：
影响因子：
5.2
通讯作者：
Breit, Bernhard
中科院分区：
文献类型：
--
作者：
Berthold, Dino;Breit, Bernhard
铑催化的三唑衍生物与内部炔烃和末端丙二烯的不对称N-1-选择性和区域选择性偶联，可以以非常好的对映选择性获得仲和叔烯丙基三唑。对于该过程，JosPOphos 配体家族的三个新成员已被制备并用于催化。优化的反应条件使得三唑能够与内部炔烃以及丙二烯偶联，表现出对官能团的高耐受性。克级反应提供了 N-1-烯丙基三唑，对其进行了各种转化，突出了合成实用性。
The rhodium-catalyzed asymmetric N-1-selective and regioselective coupling of triazole derivatives with internal alkynes and terminal allenes gives access to secondary and tertiary allylic triazoles in very good enantioselectivities. For this process, three new members of the JosPOphos ligand family have been prepared and employed in catalysis. The optimized reaction conditions enable the coupling of triazoles with internal alkynes as well as with allenes, displaying a high tolerance for functional groups. A gram scale reaction provided N-1-allyltriazole, which was subjected to various transformations highlighting synthetic utility.