Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications
Takizawa S, Gröger H, Sasai H (2015)
Chemistry 21(25): 8992-8997.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Takizawa, Shinobu;
Gröger, HaraldUniBi;
Sasai, Hiroaki
Abstract / Bemerkung
In recent years vanadium catalysis has been extended to a range of different and even complementary directions in asymmetric synthesis. Inspired by nature's way to activate both substrate and reagent in many cases, the design of efficient bifunctional and dinuclear vanadium catalysts has been achieved. Furthermore, vanadium catalysis has been an early field in which "hybrid catalysts" have been studied in detail by incorporation of oxovanadium complexes into proteins, thus giving artificial enzymes. In addition, a high compatibility of vanadium with proteins enabled the use of vanadium chemocatalysts for combinations with enzyme catalysis in one-pot, thus leading to dynamic kinetic resolutions. In this contribution, these three concepts of vanadium catalysis opening up new perspectives for asymmetric synthesis are reviewed.
Erscheinungsjahr
2015
Zeitschriftentitel
Chemistry
Band
21
Ausgabe
25
Seite(n)
8992-8997
ISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2757961
Zitieren
Takizawa S, Gröger H, Sasai H. Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications. Chemistry. 2015;21(25):8992-8997.
Takizawa, S., Gröger, H., & Sasai, H. (2015). Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications. Chemistry, 21(25), 8992-8997. doi:10.1002/chem.201406444
Takizawa, Shinobu, Gröger, Harald, and Sasai, Hiroaki. 2015. “Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications”. Chemistry 21 (25): 8992-8997.
Takizawa, S., Gröger, H., and Sasai, H. (2015). Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications. Chemistry 21, 8992-8997.
Takizawa, S., Gröger, H., & Sasai, H., 2015. Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications. Chemistry, 21(25), p 8992-8997.
S. Takizawa, H. Gröger, and H. Sasai, “Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications”, Chemistry, vol. 21, 2015, pp. 8992-8997.
Takizawa, S., Gröger, H., Sasai, H.: Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications. Chemistry. 21, 8992-8997 (2015).
Takizawa, Shinobu, Gröger, Harald, and Sasai, Hiroaki. “Vanadium in asymmetric synthesis: emerging concepts in catalyst design and applications”. Chemistry 21.25 (2015): 8992-8997.
1 Zitation in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Short Syntheses of 4-Deoxycarbazomycin B, Sorazolon E, and (+)-Sorazolon E2.
Sako M, Ichinose K, Takizawa S, Sasai H., Chem Asian J 12(12), 2017
PMID: 28418587
Sako M, Ichinose K, Takizawa S, Sasai H., Chem Asian J 12(12), 2017
PMID: 28418587
78 References
Daten bereitgestellt von Europe PubMed Central.
Rehder, Angew. Chem. Int. Ed. Engl. 30(), 1991
AUTHOR UNKNOWN, Angew. Chem. 103(), 1991
AUTHOR UNKNOWN, 0
Canali, Chem. Soc. Rev. 28(), 1999
Bolm, Coord. Chem. Rev. 237(), 2003
AUTHOR UNKNOWN, 2010
AUTHOR UNKNOWN, 0
Michaelson, J. Am. Chem. Soc. 99(), 1977
Murase, J. Org. Chem. 64(), 1999
Nakajima, Chem. Lett. (), 1986
Bolm, Angew. Chem. Int. Ed. Engl. 34(), 1996
AUTHOR UNKNOWN, Angew. Chem. 107(), 1995
Vetter, Tetrahedron Lett. 39(), 1998
Liu, J. Am. Chem. Soc. 119(), 1997
Vanadium-catalyzed asymmetric oxidation of alpha-hydroxy esters using molecular oxygen as stoichiometric oxidant.
Radosevich AT, Musich C, Toste FD., J. Am. Chem. Soc. 127(4), 2005
PMID: 15669834
Radosevich AT, Musich C, Toste FD., J. Am. Chem. Soc. 127(4), 2005
PMID: 15669834
Togni, Organometallics 9(), 1990
Vanadium-catalyzed asymmetric cyanohydrin synthesis
Belokon' YN, North M, Parsons T., Org. Lett. 2(11), 2000
PMID: 10841493
Belokon' YN, North M, Parsons T., Org. Lett. 2(11), 2000
PMID: 10841493
Blacker, Tetrahedron: Asymmetry 17(), 2006
Asymmetric Addition of Cyanide to β-Nitroalkenes Catalysed by Chiral Salen Complexes of Titanium(IV) and Vanadium(V).
North M, Watson JM., ChemCatChem 5(8), 2013
PMID: 24159364
North M, Watson JM., ChemCatChem 5(8), 2013
PMID: 24159364
Bauer, 2000
Wever, 2001
The tunichromes. A class of reducing blood pigments from sea squirts: isolation, structures, and vanadium chemistry.
Oltz EM, Bruening RC, Smith MJ, Kustin K, Nakanishi K., J. Am. Chem. Soc. 110(18), 1988
PMID: 22148795
Oltz EM, Bruening RC, Smith MJ, Kustin K, Nakanishi K., J. Am. Chem. Soc. 110(18), 1988
PMID: 22148795
Catalytic asymmetric coupling of 2-naphthols by chiral tridentate oxovanadium (IV) complexes.
Hon SW, Li CH, Kuo JH, Barhate NB, Liu YH, Wang Y, Chen CT., Org. Lett. 3(6), 2001
PMID: 11263903
Hon SW, Li CH, Kuo JH, Barhate NB, Liu YH, Wang Y, Chen CT., Org. Lett. 3(6), 2001
PMID: 11263903
Chu, Chem. Commun. (), 2001
Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates.
Barhate NB, Chen CT., Org. Lett. 4(15), 2002
PMID: 12123368
Barhate NB, Chen CT., Org. Lett. 4(15), 2002
PMID: 12123368
AUTHOR UNKNOWN, 0
The rational design of novel chiral oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols.
Luo Z, Liu Q, Gong L, Cui X, Mi A, Jiang Y., Chem. Commun. (Camb.) (8), 2002
PMID: 12123042
Luo Z, Liu Q, Gong L, Cui X, Mi A, Jiang Y., Chem. Commun. (Camb.) (8), 2002
PMID: 12123042
Novel achiral biphenol-derived diastereomeric oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols.
Luo Z, Liu Q, Gong L, Cui X, Mi A, Jiang Y., Angew. Chem. Int. Ed. Engl. 41(23), 2002
PMID: 12458529
Luo Z, Liu Q, Gong L, Cui X, Mi A, Jiang Y., Angew. Chem. Int. Ed. Engl. 41(23), 2002
PMID: 12458529
AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant.
Guo QX, Wu ZJ, Luo ZB, Liu QZ, Ye JL, Luo SW, Cun LF, Gong LZ., J. Am. Chem. Soc. 129(45), 2007
PMID: 17956093
Guo QX, Wu ZJ, Luo ZB, Liu QZ, Ye JL, Luo SW, Cun LF, Gong LZ., J. Am. Chem. Soc. 129(45), 2007
PMID: 17956093
AUTHOR UNKNOWN, 0
Shibasaki, Angew. Chem. Int. Ed. Engl. 36(), 1997
AUTHOR UNKNOWN, Angew. Chem. 109(), 1997
AUTHOR UNKNOWN, 2011
AUTHOR UNKNOWN, 0
Somei, Tetrahedron Lett. 45(), 2004
Chiral dinuclear vanadium(v) catalysts for oxidative coupling of 2-naphthols.
Takizawa S, Katayama T, Kameyama C, Onitsuka K, Suzuki T, Yanagida T, Kawai T, Sasai H., Chem. Commun. (Camb.) (15), 2008
PMID: 18379701
Takizawa S, Katayama T, Kameyama C, Onitsuka K, Suzuki T, Yanagida T, Kawai T, Sasai H., Chem. Commun. (Camb.) (15), 2008
PMID: 18379701
Takizawa, Tetrahedron 64(), 2008
Dinuclear chiral vanadium catalysts for oxidative coupling of 2-naphthols via a dual activation mechanism.
Takizawa S, Katayama T, Sasai H., Chem. Commun. (Camb.) (35), 2008
PMID: 18802502
Takizawa S, Katayama T, Sasai H., Chem. Commun. (Camb.) (35), 2008
PMID: 18802502
Takizawa, Synlett (), 2009
Vanadium-catalyzed enantioselective Friedel-Crafts-type reactions.
Takizawa S, Arteaga Arteaga F, Yoshida Y, Kodera J, Nagata Y, Sasai H., Dalton Trans 42(33), 2013
PMID: 23103937
Takizawa S, Arteaga Arteaga F, Yoshida Y, Kodera J, Nagata Y, Sasai H., Dalton Trans 42(33), 2013
PMID: 23103937
Takizawa, Tetrahedron 70(), 2014
Development of dinuclear vanadium catalysts for enantioselective coupling of 2-naphthols via a dual activation mechanism.
Takizawa S., Chem. Pharm. Bull. 57(11), 2009
PMID: 19881264
Takizawa S., Chem. Pharm. Bull. 57(11), 2009
PMID: 19881264
AUTHOR UNKNOWN, 0
Colonna, Tetrahedron: Asymmetry 3(), 1992
Colonna, Chem. Commun. (), 1997
van, J. Mol. Catal. A 117(), 1997
Adam, Adv. Biochem. Eng./Biotechnol. 63(), 1999
AUTHOR UNKNOWN, 0
Asymmetric Sulfoxidation Catalyzed by a Vanadium-Containing Bromoperoxidase.
Andersson M, Willetts A, Allenmark S., J. Org. Chem. 62(24), 1997
PMID: 11671985
Andersson M, Willetts A, Allenmark S., J. Org. Chem. 62(24), 1997
PMID: 11671985
Enantioselective Sulfoxidation Catalyzed by Vanadium Haloperoxidases.
ten Brink HB, Tuynman A, Dekker HL, Hemrika W, Izumi Y, Oshiro T, Schoemaker HE, Wever R., Inorg Chem 37(26), 1998
PMID: 11670813
ten Brink HB, Tuynman A, Dekker HL, Hemrika W, Izumi Y, Oshiro T, Schoemaker HE, Wever R., Inorg Chem 37(26), 1998
PMID: 11670813
AUTHOR UNKNOWN, 0
van, Chem. Commun. (), 1998
The rational design of semisynthetic peroxidases.
van de Velde F, Konemann L, van Rantwijk F, Sheldon RA., Biotechnol. Bioeng. 67(1), 2000
PMID: 10581439
van de Velde F, Konemann L, van Rantwijk F, Sheldon RA., Biotechnol. Bioeng. 67(1), 2000
PMID: 10581439
Biocatalytic and biomimetic oxidations with vanadium.
van de Velde F, Arends IW, Sheldon RA., J. Inorg. Biochem. 80(1-2), 2000
PMID: 10885467
van de Velde F, Arends IW, Sheldon RA., J. Inorg. Biochem. 80(1-2), 2000
PMID: 10885467
Vanadate substituted phytase: immobilization, structural characterization and performance for sulfoxidations.
Correia I, Aksu S, Adao P, Pessoa JC, Sheldon RA, Arends IW., J. Inorg. Biochem. 102(2), 2007
PMID: 18001837
Correia I, Aksu S, Adao P, Pessoa JC, Sheldon RA, Arends IW., J. Inorg. Biochem. 102(2), 2007
PMID: 18001837
Van, Top. Catal. 13(), 2000
AUTHOR UNKNOWN, 0
A dynamic kinetic resolution of allyl alcohols by the combined use of lipases and [VO(OSiPh3)3].
Akai S, Tanimoto K, Kanao Y, Egi M, Yamamoto T, Kita Y., Angew. Chem. Int. Ed. Engl. 45(16), 2006
PMID: 16544360
Akai S, Tanimoto K, Kanao Y, Egi M, Yamamoto T, Kita Y., Angew. Chem. Int. Ed. Engl. 45(16), 2006
PMID: 16544360
AUTHOR UNKNOWN, Angew. Chem. 118(), 2006
One-pot synthesis of optically active allyl esters via lipase-vanadium combo catalysis.
Akai S, Hanada R, Fujiwara N, Kita Y, Egi M., Org. Lett. 12(21), 2010
PMID: 20936813
Akai S, Hanada R, Fujiwara N, Kita Y, Egi M., Org. Lett. 12(21), 2010
PMID: 20936813
A mesoporous-silica-immobilized oxovanadium cocatalyst for the lipase-catalyzed dynamic kinetic resolution of racemic alcohols.
Egi M, Sugiyama K, Saneto M, Hanada R, Kato K, Akai S., Angew. Chem. Int. Ed. Engl. 52(13), 2013
PMID: 23424181
Egi M, Sugiyama K, Saneto M, Hanada R, Kato K, Akai S., Angew. Chem. Int. Ed. Engl. 52(13), 2013
PMID: 23424181
AUTHOR UNKNOWN, Angew. Chem. 125(), 2013
Akai, Chem. Lett. 43(), 2014
AUTHOR UNKNOWN, 0
Hussain, 2012
Ahmed, Tetrahedron 68(), 2012
Hoyos, Adv. Synth. Catal. 354(), 2012
Denard, ACS Catal. 3(), 2013
AUTHOR UNKNOWN, 0
Dinh, Tetrahedron Lett. 37(), 1996
Larsson, Angew. Chem. Int. Ed. Engl. 36(), 1997
AUTHOR UNKNOWN, Angew. Chem. 109(), 1997
Persson, J. Am. Chem. Soc. 121(), 1999
Aminocyclopentadienyl ruthenium chloride: catalytic racemization and dynamic kinetic resolution of alcohols at ambient temperature.
Choi JH, Kim YH, Nam SH, Shin ST, Kim MJ, Park J., Angew. Chem. Int. Ed. Engl. 41(13), 2002
PMID: 12203597
Choi JH, Kim YH, Nam SH, Shin ST, Kim MJ, Park J., Angew. Chem. Int. Ed. Engl. 41(13), 2002
PMID: 12203597
AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols.
Berkessel A, Sebastian-Ibarz ML, Muller TN., Angew. Chem. Int. Ed. Engl. 45(39), 2006
PMID: 16952181
Berkessel A, Sebastian-Ibarz ML, Muller TN., Angew. Chem. Int. Ed. Engl. 45(39), 2006
PMID: 16952181
AUTHOR UNKNOWN, Angew. Chem. 118(), 2006
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 25809123
PubMed | Europe PMC
Suchen in
Google Scholar