Lewis Acids Promoted 3+2 Cycloaddition of Oxaziridines and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates
文献类型：期刊论文
| 作者 | Zhao, Erbao2,3; Zhou, Feilong3; Zhao, Yujun1,3
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2019-04-05 |
| 卷号 | 84期号:7页码:4282-4293 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.9b00246 |
| 通讯作者 | Zhao, Yujun(yjzhao@simm.ac.cn) |
| 英文摘要 | Syntheses of isoxazolidines through the carbonyl imine intermediates are currently limited to monosubstituted olefin substrates. Herein, we reported syntheses of novel bicyclic isoxazolidine-containing compounds through 1,3-dipolar cycloaddition reactions using cyclic allylic alcohols as substrates, which proved challenging in previous reports. Generally, the reaction yields range from good to high, and the reaction substrates tolerate various functional groups, including the cyclopropyl and amine groups. Mechanistic studies suggest that an allylic cation and a carbonyl imine intermediate are involved and responsible for the observed stereochemistry and diastereoselectivity. |
| WOS关键词 | ACETYLENIC BOND PARTICIPATION ; BIOGENETIC-LIKE CYCLIZATION ; 1,3-DIPOLAR CYCLOADDITIONS ; OLEFINIC CYCLIZATIONS ; NITROALKANE SOLVENTS ; STEROID NUCLEUS ; ISOXAZOLIDINE ; NITRONES ; ALKALOIDS ; ATELOPUS |
| 资助项目 | National Natural Science Foundation of China[81673295] ; National Natural Science Foundation of China[81872724] ; Shanghai Institute of Materia Medica start-up grant ; K. C. Wong Education Foundation |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000464250800051 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/289976]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Zhao, Yujun |
| 作者单位 | 1.Yancheng Teachers Univ, Sch Pharm, Yancheng 224007, Jiangsu, Peoples R China 2.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Jiangsu, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhao, Erbao,Zhou, Feilong,Zhao, Yujun. Lewis Acids Promoted 3+2 Cycloaddition of Oxaziridines and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(7):4282-4293. |
| APA | Zhao, Erbao,Zhou, Feilong,&Zhao, Yujun.(2019).Lewis Acids Promoted 3+2 Cycloaddition of Oxaziridines and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates.JOURNAL OF ORGANIC CHEMISTRY,84(7),4282-4293. |
| MLA | Zhao, Erbao,et al."Lewis Acids Promoted 3+2 Cycloaddition of Oxaziridines and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates".JOURNAL OF ORGANIC CHEMISTRY 84.7(2019):4282-4293. |
入库方式： OAI收割
来源：上海药物研究所
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