Asymmetric Three-Component Strecker Reactions Catalyzed by<i>trans</i>-4-Hydroxy-L-proline-Derived<i>N</i>,<i>N′</i>-Dioxides
作者:Yuehong Wen、Bo Gao、Yingzi Fu、Shunxi Dong、Xiaohua Liu、Xiaoming Feng
DOI:10.1002/chem.200800319
日期:2008.7.28
Novel trans-4-hydroxy-L-proline-derived N,N'-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes were found to be suitable substrates. The corresponding alpha-amino nitriles were obtained in high yields with up to 95 % ee (ee=enantiomeric excess)
已开发出新型的反式-4-羟基-L-脯氨酸衍生的N,N'-二氧化物并将其用作与醛,(1,1-二苯基)甲胺和TMSCN。发现芳族和脂族醛都是合适的底物。在温和条件下,以高达95%ee(ee =对映体过量)的高收率获得了相应的α-氨基腈。在单次重结晶后可获得光学纯的产物。该催化剂可以容易地由反式-4-羟基-L-脯氨酸和二胺分三步制备。根据实验结果和观察到的产物的绝对构型,提出了一种可能的过渡态来解释不对称感应的起源。