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
Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
, p. 5054 - 5059 (2021/07/20)
An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
Acid-promoted rearrangement of α,β-epoxy acylates: Remarkable effects of an acyl group and a Lewis acid
Kita, Yasuyuki,Kitagaki, Shinji,Yoshida, Yutaka,Mihara, Sachiko,Fang, Dai-Fei,Fujioka, Hiromichi
, p. 1061 - 1064 (2007/10/03)
Remarkable steric and electrostatic effects of acyl groups and exceptionally bulky Lewis acid, (MABR), which make the rearrangement reaction applicable to various types of reaction systems including acyclic ones in the acid-promoted rearrangement of α,β-epoxy acylates, were found.
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.