Titanium-mediated reductive cross-coupling reactions of imines with terminal alkynes: An efficient route for the synthesis of stereodefined allylic amines

被引：5

作者：

Mao, Kebin ^{[1
,2
]}

Fan, Guoqin ^{[1
]}

Liu, Yuanhong ^{[1
]}

Li, Shi ^{[1
]}

You, Xu ^{[1
]}

Liu, Dan ^{[2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Shenyang Univ Chem Technol, Coll Chem Engn, Shenyang 110142, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

基金：

中国国家自然科学基金;

关键词：

allylic amine; azatitanacyclopentene; reductive cross-coupling; regioselectivity; terminal alkyne; titanium-imine complex; IN-SITU GENERATION; ASYMMETRIC-SYNTHESIS; COMPLEXES; AMINATION; ALLYLAMINE; ALDEHYDES; ETHER; ACID;

D O I：

10.3762/bjoc.9.69

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Low-valency titanium species, generated in situ by using Ti(OiPr)(4)/2 c-C5H9MgCl reagent, react with imines to give a titanium-imine complex that can couple with terminal alkynes to provide azatitanacyclopentenes with excellent regioselectivity. Stereodefined allylic amines are obtained in good yields after hydrolysis or iodonolysis of the corresponding azatitanacyclopentenes. When ethynylcyclopropane is used as the coupling partner to react with imines in this reaction, the initially generated allylic amine undergoes an unexpected 1,3-amino migration on silica gel during the column chromatography.

引用

页码：621 / 627

页数：7

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