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Communication | Special issue | Vol 79, No. 1, 2009, pp.347-352
Published online, 9th January, 2009
DOI: 10.3987/COM-08-S(D)15
Regioselective Ring Expansion of 3,3-Dimethylaziridin-2-carboxylate and a Photochemical Entry to the Penem Nucleus

James D. White* and Takuya Furuta

*Department of Chemistry, Oregon State University, Gilbert Hall 153, Corvallis, Oregon 97331, U.S.A.


3,3-Dimethylaziridin-2-carboxylates undergo ring expansion with thiocyanates to give a 4,4-dimethylthiazolidin-5-carboxylate as the major product. Irradiation of a N-cysteinyl-3,3-dimethylaziridin-2-carboxylate was found to give a penem in low yield, presumably via a transient thioaldehyde which added across the aziridine N-C(3) bond.