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

31 August 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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

Keywords

stereospecific reactions
hydroarylation
vicinal quaternary centers
spirocyclization
dearomatization
Bronsted acid catalysis

Supplementary materials

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Supporting Information
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Supporting Information for Brønsted Acid-Catalyzed Stereospecific Dearomative Spirocyclization of Benzothiophenyl Analogues of Tertiary cis-β-Benzylstyrenes
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Brønsted Acid-Catalyzed Stereospecific Dearomative Spirocyclization of Benzothiophenyl Analogues of Tertiary cis-β-Benzylstyrenes [opens in a new tab]
Anargul Tohti, Victoria Lerda, Benjamin Stokes journal article
Synlett

Version History

Aug 31, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-7lw6b
D O I: 10.26434/chemrxiv-2021-7lw6b [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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