Iridium-catalyzed selective N-allylation of hydrazines

被引：27
|
作者：
Matunas, R [1 ]
Lai, AJ [1 ]
Lee, C [1 ]
机构：
[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA
来源：
TETRAHEDRON | 2005年 / 61卷 / 26期
关键词：
iridium; catalysis; hydrazones; hydrazides; hydrazines; amination;
D O I：
10.1016/j.tet.2005.03.105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly chemo- and regioselective iridium-catalyzed allylic amination is described. The reaction of various hydrazones and hydrazides with allylic carbonates proceeds at ambient temperature in the presence of an [Ir(COD)Cl](2)/pyridine catalyst, ammonium iodide. and diethylzinc to afford the corresponding N-allylation products in high yields with excellent chemo- and regioselectivities. Only the more nucleophilic nitrogen of a given hydrazine, derivative undergoes the C-N bond formation to yield a branched allylic isomer as the exclusive product. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6298 / 6308
页数：11
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