Organocatalytic Asymmetric Conjugate Addition of 3-Monosubstituted Oxindoles to (E)-1,4-Diaryl-2-buten-1,4-diones: A Strategy for the Indirect Enantioselective Furanylation and Pyrrolylation of 3-Alkyloxindoles
文献类型：期刊论文
| 作者 | Liao, Yu-Hua ; Liu, Xiong-Li ; Wu, Zhi-Jun ; Du, Xi-Lin ; Zhang, Xiao-Mei ; Yuan, Wei-Cheng |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2012 |
| 卷号 | 18期号:21页码:6679-6687 |
| 关键词 | butendiones conjugate addition organocatalysis oxindoles Paal-Knorr cyclization |
| ISSN号 | 0947-6539 |
| 产权排序 | 2 |
| 通讯作者 | Yuan, WC (reprint author), Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China. |
| 英文摘要 | An asymmetric conjugate addition of 3-monosubstituted oxindoles to a range of (E)-1,4-diaryl-2-buten-1,4-diones, catalyzed by commercially available cinchonine, is described. This organocatalytic asymmetric reaction affords a broad range of 3,3'-disubstituted oxindoles that contain a 1,4-dicarbonyl moiety and vicinal quaternary and tertiary stereogenic centers in high-to-excellent yields (up to 98?%), with excellent diastereomeric and moderate-to-high enantiomeric ratios (up to 99:1 and 95:5, respectively). Subsequently, cyclization of the 1,4-dicarbonyl moiety in the resultant Michael adducts under different PaalKnorr conditions results in two new kinds of 3,3'-disubstituted oxindoles3-furanyl- and 3-pyrrolyl-3-alkyl-oxindolesin high yields and good enantioselectivities. Notably, the studies presented here sufficiently confirm that this two-step strategy of sequential conjugate addition/PaalKnorr cyclization is not only an attractive method for the indirect enantioselective heteroarylation of 3-alkyloxindoles, but also opens up new avenues toward asymmetric synthesis of structurally diverse 3,3'-disubstituted oxindole derivatives. |
| 学科主题 | Chemistry |
| 收录类别 | SCI |
| 资助信息 | National Natural Science Foundation of China [20802074]; National Basic Research Program of China (973 Program) [2010CB833300] |
| 语种 | 英语 |
| WOS记录号 | WOS:000304045000036 |
| 公开日期 | 2013-07-03 |
| 源URL | [http://210.75.237.14/handle/351003/23898]  |
| 专题 | 成都生物研究所_天然产物研究 |
| 推荐引用方式 GB/T 7714 | Liao, Yu-Hua,Liu, Xiong-Li,Wu, Zhi-Jun,et al. Organocatalytic Asymmetric Conjugate Addition of 3-Monosubstituted Oxindoles to (E)-1,4-Diaryl-2-buten-1,4-diones: A Strategy for the Indirect Enantioselective Furanylation and Pyrrolylation of 3-Alkyloxindoles[J]. CHEMISTRY-A EUROPEAN JOURNAL,2012,18(21):6679-6687. |
| APA | Liao, Yu-Hua,Liu, Xiong-Li,Wu, Zhi-Jun,Du, Xi-Lin,Zhang, Xiao-Mei,&Yuan, Wei-Cheng.(2012).Organocatalytic Asymmetric Conjugate Addition of 3-Monosubstituted Oxindoles to (E)-1,4-Diaryl-2-buten-1,4-diones: A Strategy for the Indirect Enantioselective Furanylation and Pyrrolylation of 3-Alkyloxindoles.CHEMISTRY-A EUROPEAN JOURNAL,18(21),6679-6687. |
| MLA | Liao, Yu-Hua,et al."Organocatalytic Asymmetric Conjugate Addition of 3-Monosubstituted Oxindoles to (E)-1,4-Diaryl-2-buten-1,4-diones: A Strategy for the Indirect Enantioselective Furanylation and Pyrrolylation of 3-Alkyloxindoles".CHEMISTRY-A EUROPEAN JOURNAL 18.21(2012):6679-6687. |
入库方式： OAI收割
来源：成都生物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。