Guanidinium ylide mediated aziridination: identification of a spiro imidazolidine-oxazolidine intermediate.
Wannaporn Disadee, Tsutomu Ishikawa, Masatoshi Kawahata, Kentaro Yamaguchi
Index: J. Org. Chem. 71(17) , 6600-3, (2006)
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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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