Versatile One-Pot Synthesis of Polysubstituted Cyclopent-2-enimines from α,ß-Unsaturated Amides: Imino-Nazarov Reaction.
Angew Chem Int Ed Engl
; 57(32): 10352-10356, 2018 08 06.
Article
en En
| MEDLINE
| ID: mdl-29924902
ABSTRACT
The imino-Nazarov cyclization of the polysubstituted pentan-1,4-diene-3-imines was realized. To this aim, a one-pot procedure involving reductive alkenyliminylation of α,ß-unsaturated secondary amides with potassium organotrifluoroborates, followed by acid-catalyzed imino-Nazarov cyclization of the polysubstituted pentan-1,4-diene-3-imine intermediates, was studied systematically. This mild, operationally simple, flexible, and high-yielding protocol efficiently affords polysubstituted pentan-1,4-diene-3-imines, cyclopentenimines, and α-amino cyclopentenones, which are useful scaffolds in organic synthesis. The substituent effect at the C2 position of the polysubstituted pentan-1,4-diene-3-imines was studied by means of density-functional theory calculations. Results suggested that the electron-donating group facilitates the imino-Nazarov cyclization process.
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01-internacional
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MEDLINE
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En
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Angew Chem Int Ed Engl
Año:
2018
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Article