Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines

Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines
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DOI:
10.1002/anie.200500795
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发表时间:
2005-01-01
影响因子:
16.6
通讯作者:
Yamamoto, Y
Yamamoto, Y
中科院分区:
化学1区
文献类型:
--
作者:
Asao, N;Yudha, S;Yamamoto, Y

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路易斯酸和/或过渡金属催化的碳亲核试剂与亚胺的加成反应是制备含氮有机化合物最重要的方法之一。特别是在催化剂存在下,碳亲核试剂与亚胺的直接加成反应是非常可取的,因为这是一种原子经济的方法。以前,我们报道了第一个过渡金属催化的丙二腈衍生物和简单的酮(如丙酮)与活化亚胺的直接加成反应[式(1)]。
The Lewis acid and/or transition-metal-catalyzed addition of carbon nucleophiles to imines is one of the most important methods for the preparation of nitrogen-containing organic compounds.[1] In particular, the direct addition of carbon pronucleophiles to imines in the presence of catalysts is highly desirable as it represents an atom-economical approach. Previously, we reported the first example of the transitionmetal-catalyzed direct addition of malononitrile derivatives and simple ketones, such as acetone, to activated imines [Eq.(1)].[2]