Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, China.
Org Biomol Chem. 2012 Sep 28;10(36):7429-38. doi: 10.1039/c2ob25932j.
New multifunctional chiral phosphine (phosphine-amide type) LB8 and BINOL derivative co-catalyzed asymmetric aza-MBH reaction of 5,5-disubstituted cyclopent-2-enones with N-sulfonated imines afforded the corresponding optically active adducts in good to outstanding yields with moderate to good ee's under mild conditions. The steric hindrance environment of BINOL derivatives as well as the nucleophilicity of the phosphorus center and the acidity of free OH which could significantly affect the stereochemical and chemical outcomes had been discussed, indicating the co-catalyzed system is very important to this particular asymmetric aza-MBH reaction.
新型多功能手性膦（膦酰胺型）LB8 和 BINOL 衍生物共同催化 5,5-二取代环戊-2-烯酮与 N-磺酰亚胺的不对称氮杂-MBH 反应，在温和条件下以中等至良好的对映选择性获得了相应的光学活性加合物，产率良好至优秀。BINOL 衍生物的空间位阻环境以及磷中心的亲核性和游离 OH 的酸性对手性和化学结果有显著影响，表明协同催化体系对这种特定的不对称氮杂-MBH 反应非常重要。
