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Catalytic Enantioselective Aza-pinacol Rearrangement |
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| Authors: | Yuanyuan Yu Jingwen Li Long Jiang Prof Dr Jing-Ren Zhang Prof Dr Liansuo Zu |
| Institution: | 1. School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.;2. School of Medicine, Tsinghua University, Beijing, 100084 China These authors contributed equally to this work.;3. School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing, 100084 China;4. School of Medicine, Tsinghua University, Beijing, 100084 China |
| Abstract: | The first catalytic enantioselective asymmetric aza-pinacol rearrangement is reported. The reactions are catalyzed by a chiral phosphoric acid and proceed via a highly organized transition state involving a cyclic aza-ortho-xylylene intermediate to afford the indoline structures with good to excellent enantioselectivity. The synthetic utility of this method is demonstrated by the asymmetric synthesis of a key intermediate to the natural product minfiensine and the identification of a chiral lead compound to repress antibiotic resistance. |
| Keywords: | antibiotics asymmetric catalysis aza-pinacol rearrangement indoline phosphoric acid |