Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Bronsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction
Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Bronsted Acid-Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction
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DOI：
10.1021/ja806875c
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发表时间：
2008-12-17
影响因子：
15
通讯作者：
Ishihara, Kazuaki
中科院分区：
文献类型：
--
作者：
Hatano, Manabu;Maki, Toshikatsu;Ishihara, Kazuaki
我们首次建立了从廉价的BINOL合成手性1，1 '-联萘-2，2'-二磺酸（BINSA 1）的实用方法。利用手性1-非手性，2，6-二芳基吡啶（2）的复合盐，作为一种方便的手性量身定制的有机酸-碱催化剂，在二酮和酮酯等价物与醛亚胺的Mannich反应中，实现了高效的对映选择性催化.
We have established, for the first time, a practical synthesis of chiral 1,1'-binaphthyl-2,2'-disulfonic acid (BINSA 1) from inexpensive BINOL. An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using chiral 1-achiral, 2,6-diarylpyridine (2) combined salts, which acted as convenient chiral tailor-made Bronsted acid-base organocatalysts in situ.