22118-00-9Relevant articles and documents
Regio- and stereoselective rearrangement reactions of various α,β- epoxy acylates: Suitable combination of acyl groups and Lewis acids
Kita, Yasuyuki,Yoshida, Yutaka,Kitagaki, Shinji,Mihara, Sachiko,Fang, Dai-Fei,Furukawa, Akihiro,Higuchi, Kazuhiro,Fujioka, Hiromichi
, p. 4979 - 4998 (1999)
Regio- and stereoselective rearrangement reactions of various α,β- epoxy acylates including acyclic, monocyclic and bicyclic systems occurred under a suitable combination of acyl groups (benzoyl, p-nitrobenzoyl, camphanoyl) and Lewis acids (BF3
Acid-promoted rearrangement of cyclic α,β-epoxy acylates: Stereoselective synthesis of spirocyclanes and quaternary carbon centers
Kita, Yasuyuki,Kitagaki, Shinji,Yoshida, Yutaka,Mihara, Sachiko,Fang, Dai-Fei,Kondo, Michinori,Okamoto, Sachi,Imai, Reiko,Akai, Shuji,Fujioka, Hiromichi
, p. 4991 - 4997 (2007/10/03)
The rearrangement reaction of α,β-epoxy acylates in cyclic systems was studied. The treatment of cis-derivatives with a Lewis acid afforded rearranged products via the regioselective β-cleavage of the oxirane ring due to the electron-withdrawing nature of the acyloxy group, whereas trans- derivatives enhanced the neighboring group participation to yield only a small amount of rearranged products. This rearrangement reaction proved to be useful for the construction of a variety of spirocyclane systems or quaternary carbon centers on rings and could be applied to their syntheses as optically active forms.