Zhao Bo-Liang, Lin Ye, Yan Hao-Hao, Du Da-Ming
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.
Org Biomol Chem. 2015 Dec 14;13(46):11351-61. doi: 10.1039/c5ob01749a.
A bifunctional squaramide catalysed aza-Michael/Michael cascade reaction between nitroalkenes and tosylaminomethyl enones or enoates has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chiral pyrrolidines with a broad substrate scope, giving the desired products in good yields (up to 99%) with good diastereoselectivities (up to 91 : 9 dr) and excellent enantioselectivities (up to >99% ee) under mild conditions. This protocol provides a straightforward entry to highly functionalized chiral trisubstituted pyrrolidine derivatives from simple starting materials.
已开发出一种双功能方酰胺催化的硝基烯烃与对甲苯磺酰氨基甲基烯酮或烯酸酯之间的氮杂迈克尔/迈克尔串联反应。这种有机催化串联反应能方便地合成具有广泛底物范围的高度官能化手性吡咯烷，在温和条件下以良好的产率（高达99%）、良好的非对映选择性（高达91:9 dr）和优异的对映选择性（高达>99% ee）得到所需产物。该方法提供了一条从简单起始原料直接合成高度官能化手性三取代吡咯烷衍生物的途径。
