Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters
Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters
复制标题
邻位轴向手性四取代烯和杂原子官能化季碳立构中心的远程立体控制构建
DOI：
10.1021/acs.orglett.8b03801
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Li Wenjun
中科院分区：
文献类型：
--
作者：
Zhang Pei;Huang Qiuhong;Cheng Yuyu;Li Rongshi;Li Pengfei;Li Wenjun
在手性磷酸存在下，由炔丙醇原位生成的对醌甲基化物分别与噻唑酮和吖内酯进行了直接的非对映和对映选择性1，8-共轭加成反应。远程立体控制的活化方法为构建邻位轴手性四取代联烯和杂原子功能化季碳立构中心提供了一种高效、简便的方法，拓展了手性磷酸的合成潜力。
The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, topara-quinone methides generatedin situfrom propargylic alcohols have been achieved in the presence of chiral phosphoric acids. The remote stereocontrolled activation protocol provides an efficient and facile approach for the construction of vicinal axially chiral tetrasubstituted allenes and heteroatom-functionalized quaternary carbon stereocenters, which expands the synthetic potential of chiral phosphoric acids.