Lanthanide(III)-Catalyzed Synthesis of trans -Diaminocyclopentenones from Substituted Furfurals and Secondary Amines via a Domino Ring-Opening/4π-Electrocyclization Pathway
2018; American Chemical Society; Volume: 20; Issue: 21 Linguagem: Inglês
10.1021/acs.orglett.8b02711
ISSN1523-7060
AutoresAfton Hiscox, Kauan Ribeiro, Robert A. Batey,
Tópico(s)Synthesis and Characterization of Pyrroles
ResumoA strategy toward the synthesis of trans-4,5-diaminocyclopent-2-enones is described. This core motif is embedded in the marine sponge derived alkaloids agelamadin B and nagelamide J. A variety of 2-substituted trans-4,5-diaminocyclopent-2-enones were synthesized in good to quantitative yields using lanthanide(III) catalysis. The products were formed exclusively as the trans-diastereomers via a mechanism in which the C4–C5 bond formation occurs through a 4π-conrotatory electrocyclization. The precursor 3-substituted furfurals can be readily accessed using palladium(0)-catalyzed cross-coupling between 3-bromofurfural and boronic acids, trifluoroborate salts, or alkynes.
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