Journal of Organic Chemistry 2006-08-18

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.