Efficient Synthesis of Benzospirocyclohexadienones via PIFA-Promoted Intramolecular Dearomative Spiroannulation

Xinkun An; Tingting Zhang; Haoyun Ma; Xie He; Mingan Wang

doi:10.1055/s-0043-1773493

Synthesis, Table of Contents

Synthesis 2024; 56(23): 3621-3629
DOI: 10.1055/s-0043-1773493

paper

Efficient Synthesis of Benzospirocyclohexadienones via PIFA-Promoted Intramolecular Dearomative Spiroannulation

Xinkun An

,

Tingting Zhang

,

Haoyun Ma

,

Xie He

,

Mingan Wang∗

Abstract

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Abstract

A rapid and convenient method for the synthesis of differently substituted spiro[cyclohexane-1,1′-isochromane]-2,5-dien-4-one derivatives via phenyliodine(III) bis(trifluoroacetate) (PIFA)-promoted intramolecular oxidative dearomatization at the para position is disclosed, with the aim of building a library of new spirocyclohexadienone scaffolds. Subsequently, this strategy is modified to access novel cyclohexanedienone-containing polycyclic compounds.

Key words

spirocyclic compounds - cyclohexadienones - hypervalent iodine(III) reagents - phenyliodine(III) bis(trifluoroacetate) - dearomatization

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References

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