Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives
文献类型：期刊论文
| 作者 | Chen, Hao; Yao, Erdong; Xu, Chi; Meng, Xiao; Ma, Yuguo |
| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2014 |
| 卷号 | 12期号:28页码:5102-5107 |
| ISSN号 | 1477-0520 |
| DOI | 10.1039/c4ob01052c |
| 英文摘要 | Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio-and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions. |
| 语种 | 英语 |
| WOS记录号 | WOS:000338432100008 |
| 出版者 | ROYAL SOC CHEMISTRY |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/43517]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Ma, Yuguo |
| 作者单位 | Peking Univ, Ctr Soft Matter Sci & Engn, Key Lab Polymer Chem & Phys, BNLMS,Minist Educ,Coll Chem, Beijing 100871, Peoples R China |
| 推荐引用方式 GB/T 7714 | Chen, Hao,Yao, Erdong,Xu, Chi,et al. Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2014,12(28):5102-5107. |
| APA | Chen, Hao,Yao, Erdong,Xu, Chi,Meng, Xiao,&Ma, Yuguo.(2014).Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives.ORGANIC & BIOMOLECULAR CHEMISTRY,12(28),5102-5107. |
| MLA | Chen, Hao,et al."Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives".ORGANIC & BIOMOLECULAR CHEMISTRY 12.28(2014):5102-5107. |
入库方式： OAI收割
来源：化学研究所
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