Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

Abstract

A convenient microwave irradiation protocol was utilized for the synthesis of β-ketosulfones 1–5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6–10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11–15 were synthesized in moderate yields and unexpected cyclopropanes 16–19 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential.

Mn(OAc)3 catalyzed intermolecular oxidative peroxycyclization of naphthoquinone

“…Expanding on our previous work on the synthesis of antiparasitic compound [30][31][32][33] and Mn(OAc) 3 reactivity, [34][35][36][37] we present herein the rst example of this original reactivity on 2-hydroxy-3-methylnaphthoquinone with various alkenes, under Mn(OAc) 3 catalytic conditions.…”

Recent advances in manganese(iii) acetate mediated organic synthesis

“…The aforementioned methodology has been generalized to further extent by Vanelle et al, 32 as they have recently employed a-methylstyrene and trans-stilbene as new coupling partner, and observed successful conversion to 2,3-dihydrofuran derivatives under similar reaction conditions, however the yield of the corresponding stilbene-substituted dihydrofuran were found to be lowered (12-25%), due to the formation of a cyclopropane derivative as side-product.…”

Synthesis of <i>α</i>-Naphthol and 2,4,7-Trimethyl-Quinolin-5-ol by Using Manganese (III) Acetate and Analysis of Its Antimicrobial Properties

“…have been studied in detail. Furthermore the addition-cyclization reactions of enolizable 1,3-dicarbonile compounds through Manganese (III) acetate have been studied [14]- [20].…”