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Título: | Direct Metal-Free Entry to Aminocyclobutenes or Aminocyclobutenols from Ynamides: Synthetic Applications |
Autor: | Alcaide, Benito CSIC ORCID; Almendros, Pedro CSIC ORCID ; Lázaro-Milla, C. | Palabras clave: | Amides Fluorine Small ring systems Cyclization Alkynes |
Fecha de publicación: | 2016 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 22: 8998-9005 (2016) | Resumen: | The [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 editor: | http://dx.doi.org/10.1002/chem.201601044 | URI: | http://hdl.handle.net/10261/140769 | DOI: | 10.1002/chem.201601044 | Identificadores: | doi: 10.1002/chem.201601044 issn: 0947-6539 e-issn: 1521-3765 |
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