Aspinall Helen C, Greeves Nicholas, Valla Carine
Donnan and Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, UK.
Org Lett. 2005 May 12;7(10):1919-22. doi: 10.1021/ol050256f.
A complex of samarium diiodide (SmI(2)) with tetraglyme catalyzes the intermolecular pinacol coupling of aromatic or aliphatic aldehydes at loadings of 10 mol % in the presence of Me(2)SiCl(2) and Mg. Diastereoselectivity of up to 95/5 (+/-/meso) has been achieved for aliphatic aldehydes and up to 19/81 (+/-/meso) for aromatic aldehydes. De values of up to 99% have been achieved in intramolecular pinacol coupling reactions using the SmI(2)/tetraglyme/Mg/Me(2)SiCl(2) catalytic system.
二碘化钐(SmI₂)与四甘醇二甲醚的配合物在Me₂SiCl₂和Mg存在下,以10 mol%的负载量催化芳香醛或脂肪醛的分子间频哪醇偶联反应。脂肪醛的非对映选择性高达95/5(±/内消旋),芳香醛的非对映选择性高达19/81(±/内消旋)。使用SmI₂/四甘醇二甲醚/Mg/Me₂SiCl₂催化体系,在分子内频哪醇偶联反应中,非对映体过量值(de值)高达99%。