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Synthesis 2022; 54(21): 4802-4809
DOI: 10.1055/a-1878-8272
paper

Synthesis of para-Quinone Methides via Oxidative Ring-Opening of Spiro-cyclopropanyl-cyclohexadienones

Chaoxing Cui
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
,
Jianli Wu∗
c   Medical School of Huanghe S & T University, The 666th OfZijingshan South Road, Zhengzhou, 450006, P. R. of China
,
Xixi Song∗
a   College of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China
,
Miaomiao Li∗
b   Division of Molecular Catalysis & Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China
› Author AffiliationsThis research was supported by the Key Scientific Research Project of Colleges and Universities in Henan Province (19A150049).
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Abstract

An efficient and simple IBX-promoted oxidative ring-opening of spiro-cyclopropanyl-cyclohexadienones was developed. Disubstituted para-quinone methides were obtained with good to excellent yields and high regioselectivity (33 examples, 45–90% yields). This convenient transformation provides a new method to construct significant para-quinone methides and features high efficiency, broad substrate scope, and good functional group compatibility

Key words

spiro-cyclopropanyl-cyclohexadienones - para-quinone methides - IBX - oxidation - ring opening

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1878-8272.
  • Supporting Information


Publication History

Received: 15 April 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
10 August 2022

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