Synlett 2024; 35(11): 1311-1314
DOI: 10.1055/a-1894-8726
letter

Brønsted Acid Catalyzed Stereospecific Dearomative Spirocyclization of Benzothiophenyl Analogues of Tertiary cis-β-Benzylstyrenes

Anargul Tohti
,
Victoria Lerda
,
This research was sponsored in part by the University of California, Merced, and by an award from the Hellman Faculty Fellows Fund. A version of this manuscript was deposited on ChemRxiv prior to review.[17]


Abstract

3-Substituted benzothiophenyl analogues of tertiary cis-β-benzylstyrenes undergo triflic acid catalyzed dearomative spirocyclization at room temperature to afford compounds containing vicinal quaternary centers. Hydroarylation of the styrene is a competing process that occurs preferentially within substrates possessing electron-rich styrenyl alkenes, or an indole in place of the benzothiophene.

Supporting Information



Publication History

Received: 03 June 2022

Accepted: 08 July 2022

Accepted Manuscript online:
08 July 2022

Article published online:
26 February 2024

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