Synthetic Utility of Chiral Bis(oxazolinyl)phenyl Transition-Metal Complexes

被引:37
作者
Ito, Jun-ichi [1 ]
Nishiyama, Hisao [1 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
asymmetric catalysis; oxazoline; pincer complex; rhodium; ruthenium; ASYMMETRIC TRANSFER HYDROGENATION; IRON-CATALYZED HYDROSILYLATION; REDUCTIVE ALDOL REACTION; RAY CRYSTAL-STRUCTURES; PINCER COMPLEXES; ENANTIOSELECTIVE ADDITION; CONJUGATE REDUCTION; BOND ACTIVATION; ALPHA; BETA-UNSATURATED ESTERS; STRUCTURAL-CHARACTERIZATION;
D O I
10.1055/s-0031-1290315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transition-metal complexes with a chiral bis(oxazolinyl)phenyl (Phebox) ligand can construct suitable chiral environments around metal centers. Thus far, a number of transition-metal complexes in the range of early to late metals have been prepared via transmetalation, cyclometalation, and oxidative addition. The fundamental properties and catalytic activities of the resulting Phebox complexes have been extensively investigated. In particular, the Phebox-Rh and Phebox-Ru complexes were found to serve as efficient and selective catalysts in asymmetric reactions for carbon-carbon bond formation, reduction of unsaturated bonds, and functionalization reactions. In this Account, we summarize details of the Phebox complexes in terms of preparations, coordination chemistry, and catalytic applications.
引用
收藏
页码:509 / 523
页数:15
相关论文
共 91 条
[1]   Chemo- and Stereoselective Iron-Catalyzed Hydrosilylation of Ketones [J].
Addis, Daniele ;
Shaikh, Nadim ;
Zhou, Shaolin ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthius .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) :1687-1691
[2]  
Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
[3]  
2-6
[4]   Synthesis and catalytic application of chiral 1,1′-bi-2-naphthol- and biphenanthrol-based pincer complexes:: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate [J].
Aydin, Juhanes ;
Kumar, K. Senthil ;
Sayah, Mahmoud J. ;
Wallner, Olov A. ;
Szabo, Kalman J. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4689-4697
[5]   Chiral palladium bis(phosphite) PCP-pincer complexes via ligand C-H activation [J].
Baber, R. Angharad ;
Bedford, Robin B. ;
Betham, Michael ;
Blake, Michael E. ;
Coles, Simon J. ;
Haddow, Mairi F. ;
Hursthouse, Michael B. ;
Orpen, A. Guy ;
Pilarski, Lukasz T. ;
Pringle, Paul G. ;
Wingad, Richard L. .
CHEMICAL COMMUNICATIONS, 2006, (37) :3880-3882
[6]   Osmium(II) CNN pincer complexes as efficient catalysts for both asymmetric transfer and H2 hydrogenation of ketones [J].
Baratta, Walter ;
Ballico, Maurizio ;
Chelucci, Giorgio ;
Siega, Katia ;
Rigo, Pierluigi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4362-4365
[7]   Terdentate RuX(CNN)(PP) (X = Cl, H, OR) complexes: Synthesis, properties, and catalytic activity in fast transfer hydrogenation [J].
Baratta, Walter ;
Bosco, Marco ;
Chelucci, Giorgio ;
Del Zotto, Alessandro ;
Siega, Katia ;
Toniutti, Micaela ;
Zangrando, Ennio ;
Rigo, Pierluigi .
ORGANOMETALLICS, 2006, 25 (19) :4611-4620
[8]   SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX [J].
BOLM, C ;
WEICKHARDT, K ;
ZEHNDER, M ;
RANFF, T .
CHEMISCHE BERICHTE, 1991, 124 (05) :1173-1180
[9]   Metal-Free Catalytic Boration at the β-Position of α,β-Unsaturated Compounds: A Challenging Asymmetric Induction [J].
Bonet, Amadeu ;
Gulyas, Henrik ;
Fernandez, Elena .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) :5130-5134
[10]   NCN-Pincer Metal Complexes (Ti, Cr, V, Zr, Hf, and Nb) of the Phebox Ligand (S,S)-2,6-Bis(4′-isopropyl-2′-oxazolinyl)phenyl [J].
Chuchuryukin, Alexey V. ;
Huang, Rubin ;
Lutz, Martin ;
Chadwick, John C. ;
Spek, Anthony L. ;
van Koten, Gerard .
ORGANOMETALLICS, 2011, 30 (10) :2819-2830