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Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines

Two (ONO pincer)ruthenium‐complex‐bound norvalines, Boc−[Ru(pydc)(terpy)]Nva−OMe (1; Boc=tert‐butyloxycarbonyl, terpy=terpyridyl, Nva=norvaline) and Boc−[Ru(pydc)(tBu‐terpy)]Nva−OMe (5), were successfully synthesized and their molecular structures and absolute configurations were unequivocally deter...

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Autores principales: Isozaki, Katsuhiro, Yokoi, Tomoya, Yoshida, Ryota, Ogata, Kazuki, Hashizume, Daisuke, Yasuda, Nobuhiro, Sadakane, Koichiro, Takaya, Hikaru, Nakamura, Masaharu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5069454/
https://www.ncbi.nlm.nih.gov/pubmed/26879368
http://dx.doi.org/10.1002/asia.201600045
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author Isozaki, Katsuhiro
Yokoi, Tomoya
Yoshida, Ryota
Ogata, Kazuki
Hashizume, Daisuke
Yasuda, Nobuhiro
Sadakane, Koichiro
Takaya, Hikaru
Nakamura, Masaharu
author_facet Isozaki, Katsuhiro
Yokoi, Tomoya
Yoshida, Ryota
Ogata, Kazuki
Hashizume, Daisuke
Yasuda, Nobuhiro
Sadakane, Koichiro
Takaya, Hikaru
Nakamura, Masaharu
author_sort Isozaki, Katsuhiro
collection PubMed
description Two (ONO pincer)ruthenium‐complex‐bound norvalines, Boc−[Ru(pydc)(terpy)]Nva−OMe (1; Boc=tert‐butyloxycarbonyl, terpy=terpyridyl, Nva=norvaline) and Boc−[Ru(pydc)(tBu‐terpy)]Nva−OMe (5), were successfully synthesized and their molecular structures and absolute configurations were unequivocally determined by single‐crystal X‐ray diffraction. The robustness of the pincer Ru complexes and norvaline scaffolds against acidic/basic, oxidizing, and high‐temperature conditions enabled us to perform selective transformations of the N‐Boc and C−OMe termini into various functional groups, such as alkyl amide, alkyl urea, and polyether groups, without the loss of the Ru center or enantiomeric purity. The resulting dialkylated Ru‐bound norvaline, n‐C(11)H(23)CO−l‐[Ru(pydc)(terpy)]Nva−NH‐n‐C(11)H(23) (l‐4) was found to have excellent self‐assembly properties in organic solvents, thereby affording the corresponding supramolecular gels. Ru‐bound norvaline l‐1 exhibited a higher catalytic activity for the oxidation of alcohols by H(2)O(2) than parent complex [Ru(pydc)(terpy)] (11 a).
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spelling pubmed-50694542016-11-01 Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines Isozaki, Katsuhiro Yokoi, Tomoya Yoshida, Ryota Ogata, Kazuki Hashizume, Daisuke Yasuda, Nobuhiro Sadakane, Koichiro Takaya, Hikaru Nakamura, Masaharu Chem Asian J Full Papers Two (ONO pincer)ruthenium‐complex‐bound norvalines, Boc−[Ru(pydc)(terpy)]Nva−OMe (1; Boc=tert‐butyloxycarbonyl, terpy=terpyridyl, Nva=norvaline) and Boc−[Ru(pydc)(tBu‐terpy)]Nva−OMe (5), were successfully synthesized and their molecular structures and absolute configurations were unequivocally determined by single‐crystal X‐ray diffraction. The robustness of the pincer Ru complexes and norvaline scaffolds against acidic/basic, oxidizing, and high‐temperature conditions enabled us to perform selective transformations of the N‐Boc and C−OMe termini into various functional groups, such as alkyl amide, alkyl urea, and polyether groups, without the loss of the Ru center or enantiomeric purity. The resulting dialkylated Ru‐bound norvaline, n‐C(11)H(23)CO−l‐[Ru(pydc)(terpy)]Nva−NH‐n‐C(11)H(23) (l‐4) was found to have excellent self‐assembly properties in organic solvents, thereby affording the corresponding supramolecular gels. Ru‐bound norvaline l‐1 exhibited a higher catalytic activity for the oxidation of alcohols by H(2)O(2) than parent complex [Ru(pydc)(terpy)] (11 a). John Wiley and Sons Inc. 2016-03-07 2016-04-05 /pmc/articles/PMC5069454/ /pubmed/26879368 http://dx.doi.org/10.1002/asia.201600045 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Isozaki, Katsuhiro
Yokoi, Tomoya
Yoshida, Ryota
Ogata, Kazuki
Hashizume, Daisuke
Yasuda, Nobuhiro
Sadakane, Koichiro
Takaya, Hikaru
Nakamura, Masaharu
Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title_full Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title_fullStr Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title_full_unstemmed Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title_short Synthesis and Applications of (ONO Pincer)Ruthenium‐Complex‐Bound Norvalines
title_sort synthesis and applications of (ono pincer)ruthenium‐complex‐bound norvalines
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5069454/
https://www.ncbi.nlm.nih.gov/pubmed/26879368
http://dx.doi.org/10.1002/asia.201600045
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