Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands
文献类型：期刊论文
| 作者 | Li, HJ; Tian, HY; Wu, YC; Chen, YJ; Liu, L; Wang, D; Li, CJ |
| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
 |
| 出版日期 | 2005-07-01 |
| 卷号 | 347期号:9页码:1247-1256 |
| 关键词 | Aqueous Asymmetric C-c Bond-forming Reaction Chiral Semi-crown Ligand Gallium-lewis Acid Catalyst Mukaiyama Aldol Reaction |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.200505089 |
| 英文摘要 | The combination of Ga(OTf)(3) with chiral semi-crown ligands (la-e) generates highly effective chiral gallium Lewis acid catalysts for aqueous asymmetric aldol reactions of aromatic silyl enol ethers with aldehydes. A ligand-acceleration effect was observed. Water is essential for obtaining high diastereo-selectivity and enantioselectivity. The p-phenyl substituent in aromatic silyl enol ether (2 h) plays an important role and increases the enantioselectivity up to 95% ee. Although aliphatic silyl enol ethers provided low enantioselectivities and silylketene acetal is easily hydrolyzed in aqueous alcohol, the aldol reactions of silylketene thioacetal (12) with aldehydes in the presence of gallium-Lewis acid catalysts give the beta-hydroxy thioester with reasonable yields and high diastereo- (up to 99: 1) and enantioselectivities (up to 96% ee). |
| 语种 | 英语 |
| WOS记录号 | WOS:000230866000013 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/57493]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Wang, D |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China 2.McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada |
| 推荐引用方式 GB/T 7714 | Li, HJ,Tian, HY,Wu, YC,et al. Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands[J]. ADVANCED SYNTHESIS & CATALYSIS,2005,347(9):1247-1256. |
| APA | Li, HJ.,Tian, HY.,Wu, YC.,Chen, YJ.,Liu, L.,...&Li, CJ.(2005).Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands.ADVANCED SYNTHESIS & CATALYSIS,347(9),1247-1256. |
| MLA | Li, HJ,et al."Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands".ADVANCED SYNTHESIS & CATALYSIS 347.9(2005):1247-1256. |
入库方式： OAI收割
来源：化学研究所
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