Guanidinium ylide mediated aziridination: identification of a spiro imidazolidine-oxazolidine intermediate |
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| Authors: | Disadee Wannaporn Ishikawa Tsutomu Kawahata Masatoshi Yamaguchi Kentaro |
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| Institution: | Graduate School of Pharmaceutical Sciences, Chiba University, Inage, Chiba 263-8522, Japan. |
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| Abstract: | We successfully isolated a spiro imidazolidine-oxazolidine intermediate in the reaction of guanidinium ylide mediated aziridination using alpha-bromocinnamaldehyde. X-ray crystallographic analysis unambiguously revealed that the stereogenic centers of the spiro intermediate were in a trans configuration. The role of the spiro compound as an intermediate in the aziridination reaction was confirmed by observation of its smooth chemical conversion into aziridine products. |
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