Five-Bond Cleavage in Copper-Catalyzed Skeletal Rearrangement of O-Propargyl Arylaldoximes to β-Lactams

I Nakamura, T Araki, M Terada

Index: Hatakeyama, Takuji; Hashimoto, Sigma; Ishizuka, Kentaro; Nakamura, Masaharu Journal of the American Chemical Society, 2009 , vol. 131, # 33 p. 11949 - 11963

Full Text: HTML

Citation Number: 31

Abstract

Copper-catalyzed skeletal rearrangement of O-propargyl arylaldoximes 1 produced the corresponding 4-arylidene-2-azetidinones 2 and their regioisomers 2′ in good to excellent yields. For example, the reaction of benzaldehyde O-1, 3-diphenylprop-2-ynyl oxime (1b) in the presence of 10 mol% CuBr in toluene at 100° C for 24 h gave (E)-4-benzylidene-1, 3- diphenylazetidin-2-one (2b) in 96% yield. 13C labeling experiments suggest that the ...