Abermil Nacim, Masson Géraldine, Zhu Jieping
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
J Am Chem Soc. 2008 Sep 24;130(38):12596-7. doi: 10.1021/ja805122j. Epub 2008 Aug 26.
The aza-MBH reaction of imines 1 and beta-naphthyl acrylate 2 in the presence of C-6' modified beta-isocupreidine derivative 1c (0.1 equiv) and beta-naphthol 5 (0.1 equiv) afforded the corresponding (3S)-aza-MBH adducts 4 in high yield and excellent enantiomeric excess. These catalytic conditions allowed the aliphatic imines to be employed for the first time as electrophilic partners of the aza-MBH reaction. The coexistence of two H-bond donors with different acidic strengths was found to be crucial for the observed high enantioselectivity.
在C-6'修饰的β-异铜试剂衍生物1c（0.1当量）和β-萘酚5（0.1当量）存在下，亚胺1与丙烯酸β-萘酯2发生氮杂-MBH反应，以高产率和优异的对映体过量得到相应的(3S)-氮杂-MBH加合物4。这些催化条件首次允许脂肪族亚胺用作氮杂-MBH反应的亲电试剂。发现具有不同酸性强度的两种氢键供体的共存对于所观察到的高对映选择性至关重要。
