PPh(3)·HBr-DMSO mediated expedient synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters and α-bromo enals: application to the synthesis of 2-methylsulfanyl-3(2H)-furanones

Chemistry : a European Journal
Kanchan MalIndrajit Das

Abstract

An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3 ⋅HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl3 -catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described.

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Citations

May 12, 2017·The Journal of Organic Chemistry·Sho InagakiTomikazu Kawano
Jul 31, 2019·Organic & Biomolecular Chemistry·Shaohua JiangXiuwen Chen
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ekaterina A VerochkinaIgor B Rozentsveig
May 20, 2015·The Journal of Organic Chemistry·Kanchan MalIndrajit Das
Jul 23, 2019·The Journal of Organic Chemistry·Zhouli HuWei Huang
Oct 29, 2021·The Journal of Organic Chemistry·Yue ShiXu Zhang

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