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

Chaoxing Cui; Jianli Wu; Xixi Song; Miaomiao Li

doi:10.1055/a-1878-8272

Synthesis, Inhaltsverzeichnis

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

^aCollege of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China

,

Jianli Wu∗

^cMedical School of Huanghe S & T University, The 666th OfZijingshan South Road, Zhengzhou, 450006, P. R. of China

,

Xixi Song∗

^aCollege of Chemistry, Zhengzhou University, No. 100 Science Avenue, Zhengzhou, 450001, P. R. of China

,

Miaomiao Li∗

^bDivision of Molecular Catalysis & Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China

› Institutsangaben

Abstract

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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

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