Regioselective alpha-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins
文献类型：期刊论文
| 作者 | Lan, Yu2; Wu, Bo1; Yu, Zhaoyuan2; Gao, Xiang1; Zhou, Yong-Gui1 |
| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2017-03-27 |
| 卷号 | 56期号:14页码:4006-4010 |
| 关键词 | Asymmetric Catalysis Butenolides Dihydrocoumarins Nucleophilic Addition Ortho-quinone Methides |
| ISSN号 | 1433-7851 |
| DOI | 10.1002/anie.201700437 |
| 文献子类 | Article |
| 英文摘要 | The enantioselective alpha-addition of deconjugated butenolides has rarely been exploited, in contrast to the well-studied gamma-addition of deconjugated butenolides. In this study, an unprecedented asymmetric alpha-addition/transesterification of deconjugated butenolides with ortho-quinone methides generated in situ afforded a series of functionalized 3,4-dihydrocoumarins containing two contiguous stereogenic centers with excellent diastereo- and enantioselectivity. DFT calculations suggested that the rarely observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic dienolate and the electrophilic ortho-quinone methide. |
| WOS关键词 | O-QUINONE METHIDES ; GAMMA-SUBSTITUTED BUTENOLIDES ; VINYLOGOUS MICHAEL REACTIONS ; DIELS-ALDER REACTION ; ASYMMETRIC-SYNTHESIS ; NATURAL-PRODUCTS ; G-QUADRUPLEX ; CONJUGATE ADDITION ; ALKYLATING-AGENTS ; ORGANIC-SYNTHESIS |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000397346200042 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://cas-ir.dicp.ac.cn/handle/321008/169472]  |
| 专题 | 大连化学物理研究所_中国科学院大连化学物理研究所 |
| 通讯作者 | Lan, Yu; Zhou, Yong-Gui |
| 作者单位 | 1.Chinese Acad Sci, State Key Lab Catalysis, Dalian Inst Chem Phys, Dalian 116023, Peoples R China 2.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China |
| 推荐引用方式 GB/T 7714 | Lan, Yu,Wu, Bo,Yu, Zhaoyuan,et al. Regioselective alpha-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2017,56(14):4006-4010. |
| APA | Lan, Yu,Wu, Bo,Yu, Zhaoyuan,Gao, Xiang,&Zhou, Yong-Gui.(2017).Regioselective alpha-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,56(14),4006-4010. |
| MLA | Lan, Yu,et al."Regioselective alpha-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.14(2017):4006-4010. |
入库方式： OAI收割
来源：大连化学物理研究所
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