Inherently chiral calix[4]arene-based bifunctional organocatalysts for enantioselective aldol reactions
文献类型：期刊论文
| 作者 | Xu, Zhen-Xiang1,2; Li, Guang-Ke1,2; Chen, Chuan-Feng1; Huang, Zhi-Tang1 |
| 刊名 | TETRAHEDRON
 |
| 出版日期 | 2008-09-08 |
| 卷号 | 64期号:37页码:8668-8675 |
| 关键词 | Inherently Chiral Calix[4]Arene Organocatalyst Enantioselective Aldol Reaction |
| ISSN号 | 0040-4020 |
| DOI | 10.1016/j.tet.2008.07.001 |
| 英文摘要 | Two optical pure m-dimethylamino substituted inherently chiral calix[4]arene derivatives 8a and 8b bearing an L-prolinamido group have been synthesized by two routes, and structurally studied by the usual spectroscopic methods and X-ray crystallographic analysis. It was found that both of 8a and 8b could be utilized as bifunctional organocatalysts to efficiently promote the aldol reactions between aromatic aldehydes and ketones in the presence of acetic acid. Especially, with 8a as the catalyst, the reaction between 4-nitrobenzaldehyde and cyclopentanone at -20 degrees C gave the anti-aldol product up to 94% ee, while the anti-aldol product in up to 94:6 dr and 79% ee was obtained when 4-cyanobenzaldehyde was used as the aldol donor. Moreover, it was also demonstrated that the inherently chiral calixarene skeleton with (cS)-conformation in 8a was identified as the matched configuration of the stereogenic elements, and the inherently chiral moiety might play an important role in helping to stereocontrol the reaction. (c) 2008 Elsevier Ltd. All rights reserved. |
| 语种 | 英语 |
| WOS记录号 | WOS:000258841100011 |
| 出版者 | PERGAMON-ELSEVIER SCIENCE LTD |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/65675]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Huang, Zhi-Tang |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xu, Zhen-Xiang,Li, Guang-Ke,Chen, Chuan-Feng,et al. Inherently chiral calix[4]arene-based bifunctional organocatalysts for enantioselective aldol reactions[J]. TETRAHEDRON,2008,64(37):8668-8675. |
| APA | Xu, Zhen-Xiang,Li, Guang-Ke,Chen, Chuan-Feng,&Huang, Zhi-Tang.(2008).Inherently chiral calix[4]arene-based bifunctional organocatalysts for enantioselective aldol reactions.TETRAHEDRON,64(37),8668-8675. |
| MLA | Xu, Zhen-Xiang,et al."Inherently chiral calix[4]arene-based bifunctional organocatalysts for enantioselective aldol reactions".TETRAHEDRON 64.37(2008):8668-8675. |
入库方式： OAI收割
来源：化学研究所
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