Meng Xueling, Yang Binmiao, Zhang Linxing, Pan Guangyao, Zhang Xinhao, Shao Zhihui
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
Lab of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics , Peking University, Shenzhen Graduate School , Shenzhen 518055 , China.
Org Lett. 2019 Mar 1;21(5):1292-1296. doi: 10.1021/acs.orglett.8b04051. Epub 2019 Feb 13.
The first metal/organo cooperatively catalyzed asymmetric reaction of C-alkynyl N-Boc-protected N,O-acetals with in situ generated oxonium ylides has been developed. This new type of propargylation allows for the efficient synthesis of structurally diverse unreported chiral propargylamines bearing oxa-quaternary stereocenters. The reaction features unprecedented substrate scope and high diastereo- and enantioselectivity. Theoretical studies suggest a novel cooperative catalysis model and the unique transfer of ROH.
首次开发了金属/有机协同催化的C-炔基N-Boc保护的N,O-缩醛与原位生成的氧鎓叶立德的不对称反应。这种新型的炔丙基化反应能够高效合成结构多样的、含有氧杂季碳立体中心的未报道过的手性炔丙胺。该反应具有前所未有的底物范围以及高非对映选择性和对映选择性。理论研究提出了一种新型的协同催化模型以及ROH的独特转移方式。
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