Enantioselective iridium-catalyzed allylic amination of ammonia and convenient ammonia surrogates
Enantioselective iridium-catalyzed allylic amination of ammonia and convenient ammonia surrogates
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DOI：
10.1021/ol701562p
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发表时间：
2007-09-27
期刊：
影响因子：
5.2
通讯作者：
Hartwig, John F.
中科院分区：
文献类型：
--
作者：
Pouy, Mark J.;Leitner, Andreas;Hartwig, John F.
氨作为亲核试剂的铱催化的不对称烯丙基化反应以立体选择性发生以形成对称的二烯丙基胺，并且廉价的氨当量三氟乙酰胺钾或高反应性的氨当量二叔丁基亚氨基二羧酸锂的相关烯丙基化反应以高产率、高支链至线性区域选择性和高对映体过量形成一系列方便保护的α-支链伯烯丙基胺。氨当量的反应用由含有单一立体化学元素的亚磷酰胺产生的催化剂进行。
Iridium-catalyzed, asymmetric allylation of ammonia as a nucleophile occurs with stereoselectivity to form a symmetric diallylamine, and related allylation of the inexpensive ammonia equivalent potassium trifluoroacetamide or the highly reactive ammonia equivalent lithium di-tert-butyliminodicarboxylate forms a range of conveniently protected, primary, a-branched allylic amines in high yields, high branched-to-linear regioselectivities, and high enantiomeric excess. The reactions of ammonia equivalents were conducted with a catalyst generated from a phosphoramidite containing a single stereochemical element.