Carbonylation of Propargyl Carbamates with Palladium(II) Bisoxazoline Catalysts: Efficient Synthesis of 5-Methoxy-3(2H)-furanones†
Dr. Taichi Kusakabe
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorTakeo Takahashi
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorRong Shen
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorAyumi Ikeda
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorYogesh Daulat Dhage
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan)
Search for more papers by this authorDr. Yuichro Kanno
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorProf. Dr. Yoshio Inouye
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorProf. Dr. Hiroaki Sasai
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan)
Search for more papers by this authorProf. Dr. Tomoyuki Mochida
Department of Chemistry, Faculty of Sciences, Kobe University, Rokkodai, Nada, Kobe 657-8501 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Keisuke Kato
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)Search for more papers by this authorDr. Taichi Kusakabe
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorTakeo Takahashi
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorRong Shen
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorAyumi Ikeda
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorYogesh Daulat Dhage
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan)
Search for more papers by this authorDr. Yuichro Kanno
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorProf. Dr. Yoshio Inouye
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Search for more papers by this authorProf. Dr. Hiroaki Sasai
The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047 (Japan)
Search for more papers by this authorProf. Dr. Tomoyuki Mochida
Department of Chemistry, Faculty of Sciences, Kobe University, Rokkodai, Nada, Kobe 657-8501 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Keisuke Kato
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510 (Japan)Search for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research (C) (No. 24590026).
Graphical Abstract
Palladium and CO: Carbonylation of 1 with [Pd(tfa)2(±)-L1] (tfa=trifluoroacetate) affords the spirofuranone 2 with inversion of the stereochemistry at C17 in 96 % yield. C17-epi-1 also gave the same product 2 with retention of the stereochemistry at C17. Labelling studies show that 13CO was incorporated into the C5′ position of the furanone ring. The first asymmetric version of this new reaction was achieved.
Supporting Information
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