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Título

Direct Metal-Free Entry to Aminocyclobutenes or Aminocyclobutenols from Ynamides: Synthetic Applications

AutorAlcaide, Benito ; Almendros, Pedro ; Lázaro-Milla, C.
Palabras claveAmides
Fluorine
Small ring systems
Cyclization
Alkynes
Fecha de publicación2016
EditorJohn Wiley & Sons
CitaciónChemistry - A European Journal 22: 8998-9005 (2016)
ResumenThe [2+2] cycloaddition of ynamides with the highly polarized reagent TfC=CHhas been developed to regioselectively afford bis(triflyl)aminocyclobutenes in the absence of catalyst under mild conditions. Incidentally, with the ynamides bearing electron-rich aromatic rings at the C-terminal, an interesting reactivity switch was observed; a cyclization/hydroxylation sequence yielded 2-amino-3-(triflyl)cyclobut-2-enols. Aminocyclobutene construction with addition of alcohols resulted in the formation of aminocyclobutenyl ethers through a cyclization/hydroalkoxylation process. Moreover, the utility of functionalized aminocyclobutenes as precursors for further elaboration was demonstrated with the preparation of α-amino-β,γ-unsaturated ketones and 3-(triflyl)buta-1,3-dien-2-amines through 4 π-electrocyclic ring opening.
Versión del editorhttp://dx.doi.org/10.1002/chem.201601044
URIhttp://hdl.handle.net/10261/140769
DOI10.1002/chem.201601044
Identificadoresdoi: 10.1002/chem.201601044
issn: 0947-6539
e-issn: 1521-3765
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