1448849-23-7Relevant academic research and scientific papers
Lewis acid-promoted cyclization reactions of alkenyl ethenetricarboxylates: Stereoselective synthesis of 2-oxotetrahydrofurans and 2-oxopyrrolidines
Yamazaki, Shoko,Fujinami, Ken,Maitoko, Yuki,Ueda, Khota,Kakiuchi, Kiyomi
, p. 8405 - 8416 (2013)
Lewis acid-promoted intramolecular reactions of alkenyl ethenetricarboxylates and the corresponding amides have been examined. Reaction of allyl ethenetricarboxylates and the amides with Lewis acids (1-2 equiv) such as TiCl4, TiBr4, AlCl3, and AlBr3 gave 3,4-trans-halogenomethyl 2-oxotetrahydrofuran and pyrrolidine derivatives stereoselectively in high yields. The stereochemistries were determined by NOE experiments. Reaction of alkyl-substituted allylic ethenetricarboxylates with Lewis acids gave chloro 2-oxotetrahydrofurans and pyrans. For some alkyl-substituted substrates, cationic intermediates may be formed under the reaction conditions, and rearranged products have been obtained.
