Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes
文献类型：期刊论文
| 作者 | Bai, Bing2,3; Zhu, Hua-Jie1,2; Pan, Wei2 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2012-08-26 |
| 卷号 | 68期号:34页码:6829-6836 |
| 关键词 | Biscarboline N Allylation Enantioselective catalysis N '-Dioxide |
| ISSN号 | 0040-4020 |
| 通讯作者 | Zhu, HJ (reprint author), Hebei Univ, Coll Life Sci, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China.,zhuhuajie@hotmail.com |
| 英文摘要 | A series of new axially chiral 1,1'-biscarboline-N,N'-dioxide Lewis base organocatalysts were examined in the asymmetric allylation of aldehydes with allyltrichlorosilane. The chiral catalysts (R)-1a-e bearing ester groups in 3,3' position provided good yields of the homoallyl alcohols with excellent enantioselectivities up to 99% for a broad substrate scope that covers aliphatic, aromatic, heteroaromatic, and alpha,beta-unsaturated aldehydes. Solvent effects on the conversion and enantioselectivity were elucidated, and CH2Cl2 proved to be the optimal solvent for the reactions. In addition, the allylation with crotyltrichlorosilane was explored and the result showed that anti-isomer was favored from (E)-crotyltrichlorosilane with complete diastereoselectivity. (C) 2012 Elsevier Ltd. All rights reserved. |
| 类目[WOS] | Chemistry, Organic |
| 研究领域[WOS] | Chemistry |
| 关键词[WOS] | PYRIDINE N-OXIDES ; ATROPOISOMERIC BIPYRIDINE N,N'-DIOXIDES ; LEWIS-BASE ACTIVATION ; SILYL KETENE ACETALS ; ASYMMETRIC ALLYLATION ; AROMATIC-ALDEHYDES ; N,N-DIOXIDE DERIVATIVES ; EFFICIENT CATALYST ; ORGANOCATALYSTS ; KETONES |
| 收录类别 | SCI ; IC |
| 资助信息 | NSFC [30873141]; 973 program [2009CB522300]; Hebei University; Key State of Laboratory of Phytochemistry and Plant Resources in West Chian |
| 语种 | 英语 |
| WOS记录号 | WOS:000306981800005 |
| 公开日期 | 2012-11-30 |
| 源URL | [http://ir.kib.ac.cn:8080/handle/151853/15712]  |
| 专题 | 昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.Hebei Univ, Coll Life Sci, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China 3.Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450002, Peoples R China 4.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Bai, Bing,Zhu, Hua-Jie,Pan, Wei. Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes[J]. TETRAHEDRON,2012,68(34):6829-6836. |
| APA | Bai, Bing,Zhu, Hua-Jie,&Pan, Wei.(2012).Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes.TETRAHEDRON,68(34),6829-6836. |
| MLA | Bai, Bing,et al."Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes".TETRAHEDRON 68.34(2012):6829-6836. |
入库方式： OAI收割
来源：昆明植物研究所
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