Organocatalytic head-to-tail dimerization of methacrolein via conjugate addition of methanol: an alcohol activation mechanism proved by electrospray ionization mass spectrometry |
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Authors: | Shin-ichi Matsuoka Shintaro ShimakawaKoji Takagi Masato Suzuki |
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Affiliation: | Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan |
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Abstract: | The head-to-tail dimerization of methacrolein via the conjugate addition of methanol is catalyzed by various organic bases, such as an amine, phosphine, and N-heterocyclic carbene, to give 2,4-dimethyl-2-methoxymethylpentane-1,5-dial in moderate yields. Based on the interpretation of the key intermediates by electrospray ionization mass spectrometry, we propose a reaction mechanism involving the initial conjugate addition of the organic bases to methacrolein to generate a zwitterionic base followed by the activation of methanol. |
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Keywords: | Dimerization Methacrolein Organocatalysis N-Heterocyclic carbene Conjugate addition |
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