Bronsted acid-catalyzed imine amidation
Bronsted acid-catalyzed imine amidation
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DOI：
10.1021/ja0533085
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发表时间：
2005-11-16
影响因子：
15
通讯作者：
Antilla, JC
中科院分区：
文献类型：
--
作者：
Rowland, GB;Zhang, HL;Antilla, JC
本文介绍了一种新的方法，即在Brnsted酸催化下胺类亲核试剂与亚胺加成，生成保护胺类产品。简单的Brnsted酸(苯基膦酸和三氟甲磺酰亚胺)是很好的催化剂，提供了较高的胺产品收率。以2，2‘-二苯基-[3，3’-联菲]-4，4‘-二醇(VAPOL)为催化剂，成功地实现了以磺胺类化合物为亲核剂的不对称亚胺酰化反应。在这些加成中发现了良好的产率和对映体选择性(高达99%ee)。
A new method for the Brønsted acid-catalyzed addition of amide nucleophiles to imines to produce protected aminal products is described. Simple Brønsted acids (phenyl phosphinic acid and trifluoromethanesulfonimide) were shown to be excellent catalysts, providing high yields of the aminal product. A catalytic asymmetric imine amidation using sulfonamides as nucleophiles was successful when a hindered biaryl phosphoric acid catalyst derived from 2,2‘-diphenyl-[3,3‘-biphenanthrene]-4,4‘-diol (VAPOL) was used. Excellent yields and enantioselectivities were found in these additions (up to 99% ee).