Mn(OAc)(3) catalyzed intermolecular oxidative peroxycyclization of naphthoquinone - Aix-Marseille Université Access content directly
Journal Articles RSC Advances Year : 2017

Mn(OAc)(3) catalyzed intermolecular oxidative peroxycyclization of naphthoquinone

Abstract

Manganese(III) acetate-mediated peroxycyclization between 2-hydroxy-3-methylnaphthoquinone and various alkenes was performed to obtain dihydronaphtho[2,3-c][1,2] dioxine-5,10(3H, 10aH)-diones. The reactivity of symmetrical or unsymmetrical 1,1-disubstituted alkenes and monosubstituted alkenes allowed the synthesis of more than 50 original molecules. Focusing on the excellent reactivity of 2-hydroxy-3-methylnaphthoquinone, we describe the first example of Mn(OAc)(3) reactivity with nitro-substituted alkenes. The scope, limitations and stereochemistry of the products synthesized are discussed. Starting from monosubstituted alkenes, the instability of a pair of diastereoisomers was observed, leading to ring opening.

Dates and versions

hal-01774203 , version 1 (23-04-2018)

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Alex Meye Biyogo, Christophe Curti, Hussein El-Kashef, Omar Khoumeri, Thierry Terme, et al.. Mn(OAc)(3) catalyzed intermolecular oxidative peroxycyclization of naphthoquinone. RSC Advances, 2017, 7 (1), pp.106--111. ⟨10.1039/c6ra25138b⟩. ⟨hal-01774203⟩
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