A general organocatalyst for direct α-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions. Scope and mechanistic insights
A general organocatalyst for direct α-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions. Scope and mechanistic insights
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DOI：
10.1021/ja056120u
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发表时间：
2005-12-28
影响因子：
15
通讯作者：
Jorgensen, KA
中科院分区：
文献类型：
--
作者：
Franzén, J;Marigo, M;Jorgensen, KA
发展的一般有机催化剂的α-官能化的醛，通过烯胺中间体，提出。基于光学活性的α，α-二芳基脯氨醇硅醚，概述了该催化剂在C-C，C-N，C-F，C-Br和C-S键立体异构形成中的应用范围。所有反应都以良好到高的产率和优异的对映选择性进行。此外，我们将提出机制的洞察力的反应过程中应用非线性效应的研究，动力学分辨率，和计算调查导致的α，α-diarylprolinol甲硅烷基醚催化剂的性能的理解。
The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.