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. © 2011 Elsevier Ltd. All rights reserved.

alpha-Diketones as acyl anion equivalents: a non-enzymatic thiamine-promoted route to aldehyde ketone coupling in PEG(400) as recyclable medium

BORTOLINI, Olga;FANTIN, Giancarlo;FOGAGNOLO, Marco;GIOVANNINI, Pier Paolo;VENTURI, Valentina;PACIFICO, Salvatore;MASSI, Alessandro
2011

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. © 2011 Elsevier Ltd. All rights reserved.
2011
Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Giovannini, Pier Paolo; Venturi, Valentina; Pacifico, Salvatore; Massi, Alessandro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1505321
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