Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide | |
Chen, FX; Zhou, H; Liu, XH; Qin, B; Feng, XM; Zhang, GL; Jiang, YZ; Feng, XM, Sichuan Univ, Coll Chem, Minist Educ, Key LGreen Chem & Technol, Chengdu 610064, Peoples R China. | |
刊名 | CHEMISTRY-A EUROPEAN JOURNAL |
2004 | |
卷号 | 10期号:19页码:4790_4797 |
关键词 | Asymmetric Catalysis Cyanohydrins Double Activation Enantioselectivity Ketones |
ISSN号 | 0947-6539 |
产权排序 | 2 |
英文摘要 | Double-activation catalysis promises high catalytic efficiency in the enantioselective cyanosilylation of ketones through the combined use of a Lewis acid and a Lewis base. Catalyst systems composed of a chiral salen-A1 complex and an N-oxide have high catalytic turnovers (200 for aromatic ketones, 1000 for aliphatic ones). With these catalysts, a wide range of aliphatic and aromatic ketones were converted under mild conditions into tertiary cyanohydrin O-TMS ethers in excellent yields and with high enantioselectivities (94% ee for aromatic ketones, 90% ee for aliphatic ones). Preliminary mechanistic studies revealed that the salen-A1 complex played the role of a Lewis acid to activate the ketone and the N-oxide that of a Lewis base to activate TMSCN; that is, double activation. |
学科主题 | Chemistry, Multidisciplinary |
语种 | 英语 |
WOS记录号 | WOS:000224357100017 |
公开日期 | 2011-07-08 |
内容类型 | 期刊论文 |
源URL | [http://210.75.237.14/handle/351003/17503] |
专题 | 成都生物研究所_天然产物研究 |
通讯作者 | Feng, XM, Sichuan Univ, Coll Chem, Minist Educ, Key LGreen Chem & Technol, Chengdu 610064, Peoples R China. |
推荐引用方式 GB/T 7714 | Chen, FX,Zhou, H,Liu, XH,et al. Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide[J]. CHEMISTRY-A EUROPEAN JOURNAL,2004,10(19):4790_4797. |
APA | Chen, FX.,Zhou, H.,Liu, XH.,Qin, B.,Feng, XM.,...&Feng, XM, Sichuan Univ, Coll Chem, Minist Educ, Key LGreen Chem & Technol, Chengdu 610064, Peoples R China..(2004).Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide.CHEMISTRY-A EUROPEAN JOURNAL,10(19),4790_4797. |
MLA | Chen, FX,et al."Enantioselective cyanosilylation of ketones by a catalytic double-activation method with an aluminium complex and an N-oxide".CHEMISTRY-A EUROPEAN JOURNAL 10.19(2004):4790_4797. |
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