Synlett 2013; 24(15): 1910-1914
DOI: 10.1055/s-0033-1339473
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis, Structure, and Function of PCP Pincer Transition-Metal-Complex-Bound Norvaline Derivatives

Hikaru Takaya*
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
c   PRESTO, Japan Science and Technology Agency
,
Takashi Iwaya
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
,
Kazuki Ogata
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
,
Katsuhiro Isozaki
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
d   CREST, Japan Science and Technology Agency
,
Tomoya Yokoi
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
,
Ryota Yoshida
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
,
Nobuhiro Yasuda
e   JASRI, SPring-8, 1-1 Kouto, Sayo, Hyogo 679-5198, Japan
,
Hirofumi Seike
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
,
Toshio Takenaka
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
,
Masaharu Nakamura*
a   International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan   Fax: +81(774)383186   eMail: takaya@scl.kyoto-u.ac.jp   eMail: masaharu@scl.kyoto-u.ac.jp
b   Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
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Publikationsverlauf

Received: 22. Mai 2013

Accepted after revision: 27. Juni 2013

Publikationsdatum:
13. August 2013 (online)


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Abstract

A PCP pincer palladium-complex-bound norvaline, Boc-l-[Pd]Nva-OMe, was synthesized and fully characterized by NMR, FT-ICR-MS, and X-ray crystallography. Selective N- and C-terminus transformations of Boc-l-[Pd]Nva-OMe were performed by conventional deprotection–condensation procedures to afford lipophilic palladium-bound norvaline derivatives without metal detachment. The N-/C-bisfunctionalized palladium-bound norvaline showed self-assembly properties, as evidenced by supramolecular gel formation. The catalytic activity of the supramolecular gel was assessed in the 1,4-conjugate addition of phenylboronic acid.

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