Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction
Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction
复制标题
DOI：
10.1021/ja0500254
复制
发表时间：
2005-03-23
影响因子：
15
通讯作者：
Sasai, H
中科院分区：
文献类型：
--
作者：
Matsui, K;Takizawa, S;Sasai, H
首次用(S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL建立了高效、新颖的双功能有机催化剂，用于氮杂-森田−-Baylis-−-Hillman反应。该反应受BINOL上Lewis碱位置的影响很大。酸−碱介导的底物活化和有机催化剂构象固定的官能团被协调地执行，以促进反应的高度对映控制。
The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita−Baylis−Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid−base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol.