Premium
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( 2 H )‐furanones
Author(s) -
Mal Kanchan,
Sharma Abhinandan,
Maulik Prakas R.,
Das Indrajit
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303755
Subject(s) - chemistry , reagent , halogenation , catalysis , oxidative phosphorylation , sequence (biology) , combinatorial chemistry , organic chemistry , biochemistry
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 PPh 3 ⋅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, AuCl 3 ‐catalyzed efficient access to 3( 2H )‐furanones from the above intermediates under extremely mild conditions are described.