Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. I. Preparation of chiral ferrocenylphosphines.

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概要

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• As chiral ligands for transition metal complex catalyzed asymmetric reactions, various kinds of chiral ferrocenylphosphines, which have planar chirality due to 1,2-unsymmetrically substituted ferrocene structure and also have a functional group on the side chain of the ferrocene nucleus, were prepared. (<I>S</I>)-<I>N</I>,<I>N</I>-dimethyl-1-[(<I>R</I>)-2-(diphenylphosphino)ferrocenyl]ethylamine [(<I>S</I>)-(<I>R</I>)-PPFA], (<I>S</I>)-<I>N</I>,<I>N</I>-dimethyl-1-[(<I>R</I>)-1′,2-bis(diphenylphosphino)ferrocenyl]ethylamine [(<I>S</I>)-(<I>R</I>)-BPPFA], and their dimethylphosphino derivatives were prepared by way of lithiation of optically resolved <I>N</I>,<I>N</I>-dimethyl-1-ferrocenylethylamine. The 1-(dimethylamino)ethyl group on the ferrocenylphosphines was converted stereospecifically by nucleophilic substitution reactions into 1-methoxy-, 1-hydroxy-, 1-diphenylphosphino-, and several 1-(dialkylamino)ethyl groups. 1-Diphenylphosphino-2-(dimethylaminomethyl)ferrocene (FcPN) was optically resolved <I>via</I> its phosphine sulfide dibenzoyltartaric acid salt. The relationship between CD spectra of the chrial ferrocenylphosphines and the configuration of their planar chirality is discussed.

• 公益社団法人 日本化学会の論文

著者

• Hamada Yuji

  Department Of Materials Science And Technology Graduate School Of Engineering Sciences Kyushu Univer

• Kumada Makoto

  Department Of Applied Chemistry And Chemical Engineering Yamaguchi University

• Yamamoto Keiji

  Department Of Applied Physics Faculty Of Engineering Tokyo University

• Matsumoto Akira

  Department Of Aeronautics And Astronautics Faculty Of Engineering Kyushu University

• Hayashi Tamio

  Department Of Chemistry Faculy Of Science Kyoto University

• Yamamoto Keiji

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Kagotani Masahiro

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Mise Takaya

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Fukushima Motoo

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Nagashima Nobuo

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Kawakami Sota

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Konishi Mitsuo

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

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