Title of article
α-Diketones as acyl anion equivalents: a non-enzymatic thiamine-promoted route to aldehyde–ketone coupling in PEG400 as recyclable medium
Author/Authors
Olga Bortolini، نويسنده , , Giancarlo Fantin، نويسنده , , Marco Fogagnolo، نويسنده , , Pier Paolo Giovannini، نويسنده , , Valentina Venturi، نويسنده , , Salvatore Pacifico، نويسنده , , Alessandro Massi Pavan b، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
6
From page
8110
To page
8115
Abstract
By mimicking the peculiar behavior of thiamine diphosphate-dependent acetylacetoin synthase, it has been demonstrated that thiamine hydrochloride 2a and its simple analogue thiazolium salt 2b are able to activate α-diketones as acyl anion equivalents in nucleophilic acylations, such as the homo-coupling of α-diketones and the hitherto unreported cross-coupling between α-diketones and α-ketoesters. These carboligation reactions were optimized under stoichiometric (2a) and catalytic conditions (2b) by using eco-friendly PEG400 as the reaction medium, thus allowing both solvent and thiazolium salt recycling.
Keywords
?-Diketones , ?-Hydroxyketones , Polyethylene glycol , Thiazolium salts , N-heterocyclic carbenes
Journal title
Tetrahedron
Serial Year
2011
Journal title
Tetrahedron
Record number
1103760
Link To Document