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Acylation of a transient Ti(IV)-enolate by acyl halides and anhydrides. Facile synthesis of α-hydroxy-β-ketoesters

Regioselective C-acylation at the carbonyl carbon of methyl phenylglyoxylate 1 occurs by reaction with a variety of acyl halides 3 and anhydrides 4 in the presence of TiCl3/py system in THF at room temperature. α-Hydroxy-β-ketoesters 5 are the only reaction products and pyridine is essential to obta...

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Bibliographic Details
Published in:Tetrahedron 1996-08, Vol.52 (33), p.11037-11044
Main Authors: Clerici, Angelo, Clerici, Laura, Porta, Ombretta
Format: Article
Language:English
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Summary:Regioselective C-acylation at the carbonyl carbon of methyl phenylglyoxylate 1 occurs by reaction with a variety of acyl halides 3 and anhydrides 4 in the presence of TiCl3/py system in THF at room temperature. α-Hydroxy-β-ketoesters 5 are the only reaction products and pyridine is essential to obtain useful yields (50–90%). The mechanism of acylation involves the intermediacy of a nucleophilic a Ti(IV)-ene diolate B. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00621-7