Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton | |
Liu, Cheng-Hang ; Yu, Zhi-Xiang | |
刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION |
2017 | |
关键词 | allenes cycloaddition density-functional calculations rhodium small ring compounds CATALYZED INTERMOLECULAR 5+2 ASYMMETRIC TOTAL-SYNTHESIS NATURAL-PRODUCT SYNTHESIS DIELS-ALDER REACTION ENE-VINYLCYCLOPROPANES VINYL AZIRIDINES 7-MEMBERED RINGS ALKYNES METAL STEREOCHEMISTRY |
DOI | 10.1002/anie.201702288 |
英文摘要 | Previously reported was that cis-ene-vinylcyclopropanes (cis-ene-VCPs) underwent Rh-catalyzed [5+2] reaction to give 5,7-fused bicyclic products, where vinylcyclopropane (VCP) acts as five-carbon synthon. Unfortunately, this reaction had very limited scope. Replacing the 2 pi component of cis-ene-VCPs to allene moiety, the corresponding cis-allene-VCPs did not undergo the expected normal [5+2] cycloaddition to give 5,7-fused bicyclic products. Instead, the challenging bicyclo[ 4.3.1]decane skeleton was obtained via an unprecedented bridged [5+2] cycloaddition. DFT calculations were applied to understand why this bridged [5+2] reaction is favored over the anticipated but not realized normal [5+2] reaction.; Natural Science Foundation of China [21672008, 21232001]; SCI(E); ARTICLE; 30; 8667-8671; 56 |
语种 | 英语 |
内容类型 | 期刊论文 |
源URL | [http://ir.pku.edu.cn/handle/20.500.11897/472117] |
专题 | 化学与分子工程学院 |
推荐引用方式 GB/T 7714 | Liu, Cheng-Hang,Yu, Zhi-Xiang. Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017. |
APA | Liu, Cheng-Hang,&Yu, Zhi-Xiang.(2017).Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. |
MLA | Liu, Cheng-Hang,et al."Rhodium(I)-Catalyzed Bridged [5+2] Cycloaddition of cis-Allene-vinylcyclopropanes to Synthesize the Bicyclo[4.3.1]decane Skeleton".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017). |
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