2006•The Journal of Organic ChemistryRequires access

Guanidinium Ylide Mediated Aziridination: Identification of a Spiro Imidazolidine-Oxazolidine Intermediate

Wannaporn Disadee, Tsutomu Ishikawa, Masatoshi Kawahata, Kentaro Yamaguchi

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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Key concepts: Imidazolidine, Oxazolidine, Aziridine, Stereocenter, Ylide, Chemistry, Stereochemistry, Organic chemistry