远程立体控制构建邻位轴向手性四取代丙二烯和杂原子官能化季碳立体中心。
Remote Stereocontrolled Construction of Vicinal Axially Chiral Tetrasubstituted Allenes and Heteroatom-Functionalized Quaternary Carbon Stereocenters.
作者信息
Zhang Pei, Huang Qiuhong, Cheng Yuyu, Li Rongshi, Li Pengfei, Li Wenjun
机构信息
Department of Medicinal Chemistry, School of Pharmacy , Qingdao University , Qingdao , 266021 , China.
Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , 518055 , China.
出版信息
Org Lett. 2019 Jan 18;21(2):503-507. doi: 10.1021/acs.orglett.8b03801. Epub 2019 Jan 8.
The direct diastereo- and enantioselective 1,8-conjugate additions of thiazolones and azlactones, respectively, to para-quinone methides generated in situ from 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.
在手性磷酸存在下，分别实现了噻唑啉酮和恶唑酮对由炔丙醇原位生成的对醌甲基化物的直接非对映和对映选择性1,8-共轭加成。这种远程立体控制的活化方案为构建邻位轴向手性四取代丙二烯和杂原子官能化的季碳立体中心提供了一种高效且简便的方法，拓展了手性磷酸的合成潜力。
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