Lewis acid-catalyzed domino generation/[2,3]-sigmatropic rearrangement of ammonium ylides to access chiral azabicycles
文献类型：期刊论文
| 作者 | Xi,Song; Dong,Jiawei; Chen,Haohua; Dong,Qiuyan; Yang,Jiao; Tan,Qiuyuan; Zhang,Changhui; Lan,Yu; Zhang,Min |
| 刊名 | SCIENCE ADVANCES
 |
| 出版日期 | 2021 |
| 卷号 | 7期号:5页码:eabd5290 |
| ISSN号 | 2375-2548 |
| DOI | 10.1126/sciadv.abd5290 |
| 英文摘要 | [2,3]-Sigmatropic rearrangement of ammonium ylides represents a fundamental reaction for stereoselective synthesis of nitrogenous compounds. However, its applicability is limited by the scarcity of efficient, catalytic, and mild methods for generating ammonium ylides. Here, we report silver-catalyzed domino generation/[2,3]-sigmatropic rearrangement of ammonium ylides, furnishing chiral azabicycles with bridgehead quaternary stereogenic centers in high enantiomeric purity (up to 99% ee). A combination of density functional theory calculations and experimental studies revealed that residual water in the reaction system is crucial for the mild reaction conditions by functioning as a proton shuttle to assist carbon-silver bond protonation and C2-H deprotonation to generate the ammonium ylide. This reaction has a broad application scope. Besides the diverse substituents, N-fused azabicycles of various ring sizes are also easily accessed. In addition to silver salts, this strategy has also been successfully implemented by using a stoichiometric amount of nonmetallic I-2. |
| WOS记录号 | WOS:000614004600022 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/73070]  |
| 专题 | 中国科学院昆明植物研究所 |
| 作者单位 | 1.Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou, Peoples R China 2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing Key Lab Theoret & Computat Chem, Chongqing, Peoples R China 3.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming, Yunnan, Peoples R China 4.Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xi,Song,Dong,Jiawei,Chen,Haohua,et al. Lewis acid-catalyzed domino generation/[2,3]-sigmatropic rearrangement of ammonium ylides to access chiral azabicycles[J]. SCIENCE ADVANCES,2021,7(5):eabd5290. |
| APA | Xi,Song.,Dong,Jiawei.,Chen,Haohua.,Dong,Qiuyan.,Yang,Jiao.,...&Zhang,Min.(2021).Lewis acid-catalyzed domino generation/[2,3]-sigmatropic rearrangement of ammonium ylides to access chiral azabicycles.SCIENCE ADVANCES,7(5),eabd5290. |
| MLA | Xi,Song,et al."Lewis acid-catalyzed domino generation/[2,3]-sigmatropic rearrangement of ammonium ylides to access chiral azabicycles".SCIENCE ADVANCES 7.5(2021):eabd5290. |
入库方式： OAI收割
来源：昆明植物研究所
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