Regioselective synthesis of trifluoromethyl group containing allylic amines by palladium-catalyzed allylic amination and sequential isomerization |
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| Authors: | Takuya HirakawaKazunori Ikeda Daiji IkedaTomoko Tanaka Hiroshi OgasaMotoi Kawatsura Toshiyuki Itoh |
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| Institution: | Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan |
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| Abstract: | The palladium-catalyzed regioselective allylic amination of the α-trifluoromethyl group-substituted allyl acetate has been accomplished using Pd(OAc)2/DPPE and Pd(π-allyl)(cod)]BF4/DPPF as catalysts. The selective formation of the γ-product was attained in the presence of Pd(OAc)2/DPPE, while the α-product was obtained using Pd(π-allyl)(cod)]BF4/DPPF. We also succeeded in the regioselective synthesis of the enantiomerically enriched aminated product from chiral allyl acetate using Pd(OAc)2/DPPE and Pd(π-allyl)(cod)]BF4/(S)-BINAP. Furthermore, we found that kinetic resolution had occurred during the isomerization step from the γ-type product to the α-type product by the Pd(π-allyl)(cod)]BF4/(S)-BINAP catalyst. |
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