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: [email protected]   Email: [email protected]
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: [email protected]   Email: [email protected]
,
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: [email protected]   Email: [email protected]
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: [email protected]   Email: [email protected]
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: [email protected]   Email: [email protected]
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: [email protected]   Email: [email protected]
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: [email protected]   Email: [email protected]
,
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: [email protected]   Email: [email protected]
,
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: [email protected]   Email: [email protected]
b  Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyoku, Kyoto 615-8510, Japan
› Author Affiliations
Further Information

Publication History

Received: 22 May 2013

Accepted after revision: 27 June 2013

Publication Date:
13 August 2013 (online)


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.

Supporting Information

 
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