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Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N '-dioxides
文献类型：期刊论文
| 作者 | Jiao, ZG ; Feng, XM ; Liu, B ; Chen, FX ; Zhang, GL ; Jiang, YZ |
| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2003 |
| 期号 | 19页码:3818_3826 |
| 关键词 | amino acids asymmetric synthesis enantioselectivity Lewis bases nitrogen oxides |
| ISSN号 | 1434-193X |
| 产权排序 | 3 |
| 通讯作者 | Feng, XM, Sichuan Univ, Coll Chem, Sichuan Key LGreen Chem & Technol, Jiuyan Bridge, Chengdu 610064, Peoples R China. |
| 中文摘要 | Axially chiral N,N'-dioxide Lewis base promoters have been developed and have for the first time been applied to the asymmetric synthesis of alpha-amino nitriles through cyanide addition to aldimines. The chiral 3,3'-dimethyl-2,2'-biquinoline N,N'-dioxide 2 exhibited high enantioselectivity for asymmetric Strecker reactions between N-benzhydrylimines and trimethylsilyl cyanide. In the presence of 1 equiv. of chiral promoter 2, the cyanosilylation of aldimines afforded the corresponding alpha-amino nitriles with ee values of up to 95%. Optically pure products (99% ee) were obtained simply by recrystallization in the cases of some of the products. Moreover, the promoter 2 could be recovered and reused at least four times without any loss of enantioselectivity and reactivity. A putative mechanism for the enantioselective Strecker reactions is also discussed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003). |
| 学科主题 | Chemistry, Organic |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000185734000015 |
| 公开日期 | 2011-07-08 |
| 源URL | [http://210.75.237.14/handle/351003/17397]  |
| 专题 | 成都生物研究所_天然产物研究 |
| 推荐引用方式 GB/T 7714 | Jiao, ZG,Feng, XM,Liu, B,et al. Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N '-dioxides[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2003(19):3818_3826. |
| APA | Jiao, ZG,Feng, XM,Liu, B,Chen, FX,Zhang, GL,&Jiang, YZ.(2003).Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N '-dioxides.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(19),3818_3826. |
| MLA | Jiao, ZG,et al."Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N '-dioxides".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .19(2003):3818_3826. |
入库方式： OAI收割
来源：成都生物研究所
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