Highly Practical BINOL-Derived Acid-Base Combined Salt Catalysts for the Asymmetric Direct Mannich-Type Reaction
Highly Practical BINOL-Derived Acid-Base Combined Salt Catalysts for the Asymmetric Direct Mannich-Type Reaction
复制标题
DOI：
10.1055/s-0030-1258296
复制
发表时间：
2010-11-01
影响因子：
2.6
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Hatano, Manabu;Ishihara, Kazuaki
乙二胺与1，3-二羰基化合物之间的催化不对称直接Mannich反应是有机化学中最重要的碳-碳键形成反应之一。在手性酸碱结合盐不对称反应的研究过程中，我们开发了一系列简单实用的手性联苯醇衍生物盐催化剂，如手性吡啶1，1‘-联萘-2，2’-二磺酸盐1，1‘-联萘酯2，手性镁(II)联萘酸酯(3)，手性磷酸钙(II)4和手性磷酸5，这些催化剂对直接Mannich反应特别有效。
The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active b-amino ketones, b-amino esters, b-lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1'-binaphthyl-2,2'-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions.