Takizawa Shinobu
The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka, Japan.
Yakugaku Zasshi. 2009 Oct;129(10):1201-10. doi: 10.1248/yakushi.129.1201.
This review describes our recent efforts in the development of acid-base organocatalysts, (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl) BINOL (6a) and (S)-3-[2-(diphenylphosphino)phenyl] BINOL (13a), with dual activation mechanism for the aza-Morita-Baylis-Hillman (aza-MBH) reaction. In these catalysts, chiral Brønsted acid units are connected with a Lewis base unit via a spacer. The acid-base moieties act cooperatively as an enzyme-mimetic catalyst to activate substrates in the carbon-carbon bond forming reaction between enones and N-tosylimines with high enantioselectivity.
本综述描述了我们最近在开发酸碱有机催化剂方面所做的工作，即（S）-3-（N-异丙基-N-3-吡啶基氨基甲基）联萘酚（6a）和（S）-3-[2-（二苯基膦基）苯基]联萘酚（13a），它们对氮杂-Morita-Baylis-Hillman（aza-MBH）反应具有双重活化机制。在这些催化剂中，手性布朗斯特酸单元通过一个间隔基与一个路易斯碱单元相连。酸碱部分协同作用，作为一种模拟酶催化剂，在烯酮与N-对甲苯磺酰亚胺之间的碳-碳键形成反应中以高对映选择性活化底物。
