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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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Published in: | Tetrahedron 1996-08, Vol.52 (33), p.11037-11044 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/0040-4020(96)00621-7 |