Department of Chemistry , Stanford University , Stanford , California 94305 , United States.
Org Lett. 2020 Feb 21;22(4):1675-1680. doi: 10.1021/acs.orglett.0c00318. Epub 2020 Feb 4.
Herein we present a Zn-ProPhenol-catalyzed double Mannich reaction between ynones and imines that generates 1,3-diamines in excellent yield as well as diastereo- and enantioselectivity (>99.5% ). With 2.2 equiv of a single imine electrophile, we obtain -symmetrical diamines whereas, with two different imine partners, we obtain unsymmetrically substituted 1,3-diamines with three contiguous stereocenters. In addition, we showcase the utility of these double Mannich adducts by transforming the 1,3-diamine motif into a variety of interesting products.
在这里，我们提出了一种 Zn-ProPhenol 催化的 ynones 和亚胺之间的双 Mannich 反应，该反应以优异的收率和非对映选择性和对映选择性（>99.5%）生成 1,3-二胺。使用 2.2 当量的单一亚胺亲电试剂，我们得到了对称的二胺，而使用两个不同的亚胺配体，我们得到了具有三个连续立体中心的不对称取代的 1,3-二胺。此外，我们通过将 1,3-二胺基转化为各种有趣的产物，展示了这些双曼尼希加成物的实用性。
