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

Molecules

Ahlem Bouhlel¹  Christophe Curti¹  Clémence Tabelé¹ 

[1] id="af1-molecules-18-04293">Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Aix-Marseille Univ, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, 27 Bd Jean Moulin, CS 30064, 13385 Marseille Cedex 05, Fran

关键词: manganese(III) acetate;    dihydrofuran;    radicals;   

DOI  :  10.3390/molecules18044293

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.