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Paper | Special issue | Vol 93, No. 2, 2016, pp.512-528
Published online, 28th October, 2015
DOI: 10.3987/COM-15-S(T)22
Pd(II)-Catalyzed Ligand-Controlled Synthesis of 2,3-Dihydroisoxazole-4-carboxylates and Bis(2,3-dihydroisoxazol-4-yl)methanones

Tomohiro Ariyama, Taichi Kusakabe,* Keita Sato, Mifuyu Funatogawa, Dong Lee, Keisuke Takahashi, and Keisuke Kato*

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Pd(II)-catalyzed ligand-controlled switching between cyclization–carbonylation and cyclization–carbonylation–cyclization-coupling (CCC-coupling) reactions of propargylic N-hydroxylamines was investigated. The use of a [Pd(tfa)2(box)] catalyst in MeOH afforded symmetric ketones bearing two 2,3-dihydroisoxazoles in good yields; replacing the catalyst and solvent with Pd(tfa)2 and MeOH/DMSO led to the formation of methyl 2,3-dihydroisoxazole -4-carboxylates in good yields.