A two-step four-component queuing cascade involving a Heck coupling, π-allylpalladium trapping and Diels-Alder reaction

Baris Yücel, Lars Arve, Armin De Meijere*

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17 Atıf (Scopus)

Özet

Palladium-catalyzed cross-coupling of bicyclopropylidene (1) with iodoethene (11) in the presence of a secondary amine 12 provides allylidenecyclopropanes 13 which undergo immediate Diels-Alder reactions upon addition of dienophiles 14-18 to provide 8-(1′-aminoethyl)-substituted spiro[2.5]oct-7-ene derivatives 23a-26a in 29-66% yield. The same one-pot, two-step queuing cascade can be carried out with other iodoalkenes including cyclic ones and with cyclic dienophiles such as N-arylmaleinamides 19-22 and N-phenyl-triazolinedione 37 to furnish highly substituted spiro[2.5]oct-4-enes and spirocyclopropanated heterobicycles 47a-49a, 41a-46a (17-50%). Spirocyclopropanated heterobicycles such as 55, 56 (25 and 38% yield, respectively) can also be obtained by an inter-intra-intra-intermolecular version of this queuing cascade involving 1-hydroxyethyl- and 1-aminoethyl-substituted iodoethenes 53, 54.

Orijinal dilİngilizce
Sayfa (başlangıç-bitiş)11355-11373
Sayfa sayısı19
DergiTetrahedron
Hacim61
Basın numarası48
DOI'lar
Yayın durumuYayınlandı - 28 Kas 2005
Harici olarak yayınlandıEvet

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