Two routes are examined to achieve the synthesis of a glutarimide possessing a quaternary asymmetric centre with good stereocontrol. It appears that the first one, involving enantioselective Michael addition of cyano-4-(3,4-dichlorophenyl)butanoate on allyl acrylate is the most interesting in terms of cleanness of reactions and stereocontrol. The best system involves a quinidine derived catalyst at - 40°C with potassium hydroxide as a base and gave a medium ee (60%).
Keywords: phase transfer michael addition, methyl 4- cyano-4-(3,4-dichlorophenyl)butanoates, acrylates, enantioselective Michael addition
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