Synthesis of chiral 尾-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst
- 作者：Simon Jones ; simon.jones@sheffield.ac.uk ; Xianfu Li
- 关键词：Hydrosilylation ; Asymmetric synthesis ; 尾-amino acid ; Organocatalyst
- 刊名：Tetrahedron
- 出版年：2012
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：8 July, 2012
- 卷：68
- 期：27-28
- 页码：5522-5532
- 文件大小：1584 K
摘要
The organocatalysed asymmetric hydrosilylation of a number of N-aryl and alkyl 尾-substituted enamino esters proceeds in generally good yield and enantioselectivity. Crucial to obtaining high yield and selectivity was the addition of benzoic acid as an additive and under these conditions, both N-alkyl and N-aryl substituents were well tolerated. 尾-Aryl and alkyl substituents were evaluated and a model proposed to account for the experimental observations based upon enamine tautomerisation and conformational preferences of the reactive ketimine intermediate.