期刊
SYNLETT
卷 30, 期 8, 页码 967-971出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611790
关键词
allenes; amines; C-H activation; homogeneous catalysis; titanium; hydroaminoalkylation
资金
- Deutsche Forschungsgemeinschaft [DO 601/9-1]
The first examples of early-transition-metal-catalyzed hydroaminoalkylation reactions of allenes are reported. Initial studies performed with secondary aminoallenes led to the identification of a suitable titanium catalyst and revealed that under the reaction conditions, the initially formed hydroaminoalkylation products undergo an unexpected titanium-catalyzed rearrangement to form the thermodynamically more stable allylamines. The assumption that this rearrangement involves a reactive allylic cation intermediate provides a simple explanation of the fact that no successful early-transition-metal-catalyzed hydroaminoalkylations of allenes have previously been reported. As a result of the generation of the corresponding cation, the titaniumcatalyzed intermolecular hydroaminoalkylation of propa-1,2-diene unexpectedly gives an aminocyclopentane product formed by incorporation of two equivalents of propa-1,2-diene.
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