Wang Li-Ren, Chang Dan, Feng Yu, He Yan-Mei, Deng Guo-Jun, Fan Qing-Hua
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, P. R. China.
Org Lett. 2020 Mar 20;22(6):2251-2255. doi: 10.1021/acs.orglett.0c00444. Epub 2020 Feb 28.
A direct and facile construction of optically pure julolidine derivatives through ruthenium-catalyzed enantioselective cascade hydrogenation and reductive amination of 2-(quinolin-8-yl)ethyl ketones has been developed. By means of this protocol, various chiral julolidine compounds were obtained in high isolated yields (up to 94%) with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 99% ee) under mild conditions. Furthermore, the synthetic practicality of this protocol was illustrated by the preparation of hexahydrojulolidines and a chiral fluorescent molecular rotor.
通过钌催化的对映选择性级联氢化和2-(喹啉-8-基)乙基酮的还原胺化反应，实现了光学纯呫吨啶衍生物的直接简便构建。通过该方法，在温和条件下，以高分离产率（高达94%）、优异的非对映选择性（高达>20:1 dr）和对映选择性（高达99% ee）获得了各种手性呫吨啶化合物。此外，通过制备六氢呫吨啶和手性荧光分子转子，证明了该方法的合成实用性。
