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Paper | Special issue | Vol 103, No. 1, 2021, pp.379-391
Published online, 9th July, 2020
DOI: 10.3987/COM-20-S(K)21
Regiodivergent Ring Opening Reactions of 2-Arylated 3-Nitrocyclopropane-1,1-dicarboxylates Leading to Polyfunctionalized Dipoles

Haruyasu Asahara,* Rikiya Kamidate, and Nagatoshi Nishiwaki*

*Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0821, Japan

Abstract

Two kinds of Lewis acid induced ring-opening reactions of 2-aryl-3-nitrocyclopropane-1,1-dicarboxylates proceeded to afford 5-aryl-2-isoxazolines and γ-keto acid derivatives, respectively. Different ring-opening modes could be controlled by choosing the ligand or solvent.