Michael-type addition of hydroxide to alkynylselenonium salt: practical use as a ketoselenonium ylide precursor |
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Authors: | Shin-ichi Watanabe |
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Institution: | Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan |
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Abstract: | A novel synthetic method of ketodiphenylselenonium ylide from alkynylselenonium salt is described. A reaction of alkynylselenonium salt, hydroxide ion, and aldehyde in the presence of silver triflate and triethylamine gave oxiranylketones just as a trans-isomer in moderate to good yields, whereas benzoyl aziridine derivatives were obtained from the reaction with sodium p-toluenesulfonamide instead of a hydroxide ion. |
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Keywords: | Michael reactions Oxiranes Selenonium ions Ylides Aziridines |
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