Diastereoselective rhodium(II)-catalyzed sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic allylic sulfides |
| |
| Affiliation: | 1. Institute of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan 250012, PR China;2. Cyrus Tang Hematology Center, Soochow University, Suzhou, PR China;3. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki, Kagawa 769-2193, Japan;1. Materials and Chemical Engineering College, Henan Institute of Engineering, Zhengzhou, He’nan 450007, People’s Republic of China;2. College of Chemistry & Chemical Engineering, YangZhou University, YangZhou, Jiangsu 225002, People’s Republic of China;1. School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, No. 19A, YuQuan Road, Beijing 100049, PR China;2. College of Earth Science, University of Chinese Academy of Sciences, Key Laboratory of Computational Geodynamics, Chinese Academy of Sciences, Beijing 100049, PR China;1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China;2. Pharmacy School, Zunyi Medical College, Zunyi 563000, PR China;3. Wenzhou University, Wenzhou 325035, PR China;4. Shanghai University of Traditional Chinese Medicine, Shanghai 201203, PR China;5. College of Life Science, Sichuan University, Chengdu 610064, PR China |
| |
| Abstract: | The tandem sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic secondary allylic sulfides, (E)-9 and (Z)-10, is found to proceed with high diastereocontrol. The C-5 stereocenter bearing the sulfide group is essential for high diastereoselectivity in the reaction. Transition state conformers are proposed to explain the high diastereoselectivity in the formation of the diastereomeric products, 18a and 18b. The method is applied to the synthesis of (R)-4-(4-chlorophenyl)-2-butyrolactone. Modest enantioselectivity (63% ee) was achieved and this is attributed to partial racemization during the formation of the secondary allylic sulfide 22. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
