Lewis Acid-Promoted Cyclization Reactions of Alkenyl Ethenetricarboxylates: Stereoselective Synthesis of 2-Oxotetrahydrofurans and 2-Oxopyrrolidines

S Yamazaki, K Fujinami, Y Maitoko…

Index: Yamazaki, Shoko; Fujinami, Ken; Maitoko, Yuki; Ueda, Khota; Kakiuchi, Kiyomi Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8405 - 8416

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Citation Number: 6

Abstract

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- ...