铑（II）/布朗斯特酸催化原位生成的氧鎓叶立德和碳炔基N-叔丁氧羰基N,O-缩醛的通用且高度非对映和对映选择性炔丙基化反应：多官能团炔丙胺的合成
Rh(II)/Brønsted Acid Catalyzed General and Highly Diastereo- and Enantioselective Propargylation of in Situ Generated Oxonium Ylides and C-Alkynyl N-Boc N,O-Acetals: Synthesis of Polyfunctional Propargylamines.
作者信息
Meng Xueling, Yang Binmiao, Zhang Linxing, Pan Guangyao, Zhang Xinhao, Shao Zhihui
机构信息
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.
出版信息
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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