Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, USA.
J Am Chem Soc. 2010 Apr 7;132(13):4536-7. doi: 10.1021/ja100539c.
Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The helicene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).
手性螺旋 2-氨基吡啶鎓离子被设计为比常用的(硫代)脲基体系更具酸性(活性)的双氢键催化剂。螺环骨架被专门用来在催化剂的氢键侧定位一个固有的手性障碍。该催化剂的反应活性和对映选择性在 4,7-二氢吲哚与硝基烯烃的加成反应中得到了成功验证(催化剂用量为 0.5-2 摩尔%,对映选择性高达 98:2)。