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Sanjuán et al. Org Lett. 2016;18(5):1072-5. Formal %@5B4 %@2B 1%@5D Cycloadditions of β,β-Diaryl-Substituted ortho-(Alkynyl)styrenes through Gold(I)-Catalyzed Cycloisomerization Reactions.

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Org Lett. 2016 Mar 4;18(5):1072-5. doi: 10.1021/acs.orglett.6b00191.

Formal [4+1] Cycloadditions of β,β-Diaryl-Substituted ortho-(Alkynyl)styrenes through Gold(I)-Catalyzed Cycloisomerization Reactions.

Ana M Sanjuán, Cintia Virumbrales, Patricia García-García, Manuel A Fernández-Rodríguez, Roberto Sanz

Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos , Pza. Misael Bañuelos s/n, 09001-Burgos, Spain.

Abstract

Gold(I)-catalyzed cycloisomerization of β,β-diaryl-o-(alkynyl)styrenes at 80 °C selectively yields dihydroindeno[2,1-a]indenes in a transformation that encompasses a formal [4+1] cycloaddition and takes place through a cascade 5-endo-cyclization-diene activation-iso-Nazarov cyclization. In addition, by performing the reaction at 0 °C, the same substrates exclusively give rise to benzofulvene derivatives, which have also been shown to be intermediates in the formation of the tetracyclics.