Iridium-catalyzed, asymmetric amination of allylic alcohols activated by Lewis acids

被引:158
作者
Yamashita, Yasuhiro
Gopalarathnam, Apsara
Hartwig, John F.
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
[2] Univ Illinois, Sch Chem Sci, Urbana, IL 61801 USA
关键词
D O I
10.1021/ja0730718
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct, Ir-catalyzed, regio- and enantioselective amination of allylic alcohols with Lewis acid activators to form branched allylic amine products is reported. The reactions of arylamines, benzylic amines, and secondary aliphatic amines in the presence of Nb(OEt)(5) as activator occurred with high regioselectivities and high enantioselectivities. These results led to the development of Ir-catalyzed reactions of allylic alcohol with arylamines and BPh3 as activator in catalytic amounts. These reactions are rare examples of enantioselective substitutions of allylic alcohols. They are particularly unusual examples of the substitution of allylic alcohols to generate branched substitution products from monosubstituted allylic alcohols and of enantioselective substitutions of allylic alcohols with amine nucleophiles.
引用
收藏
页码:7508 / +
页数:3
相关论文
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