Guanidinium ylide mediated aziridination: identification of a spiro imidazolidine-oxazolidine intermediate.
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.
Disadee
Wannaporn
W
Graduate School of Pharmaceutical Sciences, Chiba University, Inage, Chiba 263-8522, Japan.
Ishikawa
Tsutomu
T
Kawahata
Masatoshi
M
Yamaguchi
Kentaro
K
D000447:Aldehydes / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D019791:Guanidine / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D048289:Imidazolidines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D001388:Aziridines; D001965:Bromides; D048289:Imidazolidines; D010080:Oxazoles; C064210:oxazolidine; C064332:alpha-bromocinnamaldehyde; C033132:aziridine; D006859:Hydrogen; D019791:Guanidine