DacBleda
Probably a bot.
Joined: 22 Jun 2005
Posts: 1
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 Posted: Wed Jun 22, 2005 7:13 am Post subject: Lactame + Grignard |
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 I'm trying to introduce an alkyl chain (with a primary grignard reagent) into de carbonil position of an N-alkylated pyperidone to generate the corresponding enamine (cause although the amino could act as a leaving group the resulting amino-ketone after the work-up could be cyclizated again with a Dean-Stark).
But in that case I just obtain an intermolecular by-product that could only be explained if the grignard acted as a base in the alfa-carbon instead of like a nucleophile. The reaction was tested in THF and Toluene/THF
Any idea to increase nucleophility of grignard and/or avoid the deprotonation in the alfa carbon of the amide: solvents, temperature, catalist, salts addition, etc...? 
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