Ligand-Controlled, Palladium-Catalyzed Asymmetric [4+4] and [2+4] Cycloadditions
Qiuyu Li1, Rui Pan1, Meihui Wang1
1State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Bioactive Natural Product Research, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, P. R. China.
Abstract:
Ligand-controlled, palladium-catalyzed asymmetric [4+4] and [2+4] cycloaddition reactions of benzofuran-derived azadienes have been developed. Taking advantage of chiral P,N-ligand (S,Rp)-PPFA, we obtained a variety of benzofuro[2,3-c][1,5] oxazocines in good yields with excellent enantioselectivities via [4+4] cycloaddition reactions. Employing chiral P,P-ligand (S)-Cl-MeO-BIPHEP, the chemo- and regioselectivities were switched to synthesize tetrahydropyran-fused spirocyclic compounds in good efficiency via [2+4] cycloaddition reactions.
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