Synthesis of gamma-amino- and delta-amino-functionalised ethers, amines, or silanes by hydroaminomethylation of heterofunctionalised allylic compounds

Citation
T. Rische et al., Synthesis of gamma-amino- and delta-amino-functionalised ethers, amines, or silanes by hydroaminomethylation of heterofunctionalised allylic compounds, EUR J ORG C, (3), 1999, pp. 653-660
Citations number
59
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
3
Year of publication
1999
Pages
653 - 660
Database
ISI
SICI code
1434-193X(199903):3<653:SOGADE>2.0.ZU;2-F
Abstract
Heterofunctionalised allylic ethers 1, silanes 5, and amines 9 are hydrofor mylated in the presence of primary or secondary amines 2 to form the corres ponding gamma-amino- and delta-amino- functionalised compounds. The rhodium (I)-catalysed reaction sequence proceeds by aldehyde formation and subseque nt reductive amination to generate thecorresponding functionalised secondar y or tertiary amines. This selective one-pot hydroaminomethylation procedur e establishes access to gamma-amino- and delta-amino-functionalised ethers, amines or silanes with potential biological activity.