title: 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.
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.
authors: Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032 (India), Fax: (+91) 33-2473-5197.
authors: Kanchan
authors: K
authors: Mal
authors: Abhinandan
authors: A
authors: Sharma
authors: Prakas R
authors: PR
authors: Maulik
authors: Indrajit
authors: I
authors: Das
keywords: chemoselectivity; cyclization; gold; oxidative bromination; triphenylphosphine hydrobromide