Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on water and with dihydroxyacetone in organic solvents
文献类型：期刊论文
| 作者 | Zhu, Ming-Kui1,4; Xu, Xiao-Ying1; Gong, Liu-Zhu1,2,3 |
| 刊名 | Advanced synthesis & catalysis
 |
| 出版日期 | 2008-06-01 |
| 卷号 | 350期号:9页码:1390-1396 |
| 关键词 | Aldol reaction Aqueous-phase catalysis Asymmetric catalysis Carbohydrates Hydrogen bonds Organic catalysis |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.200800105 |
| 通讯作者 | Gong, liu-zhu(gonglz@ustc.edu.cn) |
| 英文摘要 | An on-water, asymmetric, and direct synaldol reaction of aliphatic ketones with aromatic aldehydes catalyzed by a primary amino acid-based organocatalyst afforded the syn-aldol adducts in high yields with excellent diastereo- and enantioselectivities (up to > 20/1 dr, > 99% ee), and a highly enantioselective syn-aldol reaction of dihydroxyacetone with a variety of aldehydes in thf proceeded with 14/1 to > 20/1 dr and 92 to > 99% ee. water not only accelerated the reaction, but also enhanced the enantioselectivity. this positive water effect might arise from the hydrogen bond formed between a pendant hydroxy group of surface water molecules at the hydrophobic interface with the amide oxygen of the organocatalyst, which increases the acidity of the amide nh and thereby strengthens the related hydrogen bond formed with the aldehyde. |
| WOS关键词 | DIELS-ALDER REACTIONS ; ENAMINE CATALYSIS ; PROLINE ; ACID ; FLUOROACETONE ; MOLECULES ; MICHAEL ; MANNICH ; DESIGN |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Applied ; Chemistry, Organic |
| 语种 | 英语 |
| WOS记录号 | WOS:000256976100032 |
| 出版者 | WILEY-BLACKWELL |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2393200 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Gong, Liu-Zhu |
| 作者单位 | 1.Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China 2.Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China 3.Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China 4.Chinese Acad Sci, Grad Sch, Beijing, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhu, Ming-Kui,Xu, Xiao-Ying,Gong, Liu-Zhu. Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on water and with dihydroxyacetone in organic solvents[J]. Advanced synthesis & catalysis,2008,350(9):1390-1396. |
| APA | Zhu, Ming-Kui,Xu, Xiao-Ying,&Gong, Liu-Zhu.(2008).Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on water and with dihydroxyacetone in organic solvents.Advanced synthesis & catalysis,350(9),1390-1396. |
| MLA | Zhu, Ming-Kui,et al."Organocatalytic asymmetric syn-aldol reactions of aldehydes with long-chain aliphatic ketones on water and with dihydroxyacetone in organic solvents".Advanced synthesis & catalysis 350.9(2008):1390-1396. |
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来源：中国科学院大学
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