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

AuthorsAlcaide, Benito ; Almendros, Pedro ; Lázaro-Milla, C.
Small ring systems
Issue Date2016
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 22: 8998-9005 (2016)
AbstractThe [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.
Publisher version (URL)http://dx.doi.org/10.1002/chem.201601044
Identifiersdoi: 10.1002/chem.201601044
issn: 0947-6539
e-issn: 1521-3765
Appears in Collections:(IQOG) Artículos
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