Asymmetric Transfer Hydrogenation of 1-Naphthyl Ketones by an ansa-Ru(II) Complex of a DPEN-SO2N(Me)(CH2)2(n6-p-Tol) Combined Ligand

被引:44
|
作者
Kisic, Andrea [1 ]
Stephan, Michel [1 ]
Mohar, Barbara [1 ]
机构
[1] Natl Inst Chem, SI-1000 Ljubljana, Slovenia
关键词
ENANTIOSELECTIVE TRANSFER HYDROGENATION; TETHERED RUTHENIUM(II) CATALYST; BIFUNCTIONAL CATALYSIS; AROMATIC KETONES; ALCOHOLS; MECHANISM;
D O I
10.1021/ol400393j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyI)-tethered (DPEN-k(2)N,N)/n(6)toluene hybrid ligand Is introduced. Using an SIC 1000 in HCO2H Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed.
引用
收藏
页码:1614 / 1617
页数:4
相关论文
共 50 条
  • [1] ansa-Ruthenium(II) Complexes of DPEN-SO2N(Me)(CH2)n(η6-aryl) Conjugate Ligands for Asymmetric Transfer Hydrogenation of Aryl Ketones
    Kisic, Andrea
    Stephan, Michel
    Mohar, Barbara
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3193 - 3198
  • [2] ansa-Ruthenium(II) Complexes of R2NSO2DPEN-(CH2)n(6-Aryl) Conjugate Ligands for Asymmetric Transfer Hydrogenation of Aryl Ketones
    Kisic, Andrea
    Stephan, Michel
    Mohar, Barbara
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) : 2540 - 2546
  • [3] Mechanism of Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by a Combined System of Ru(π-CH2C(CH3)CH2)2(cod) and the Chiral sp2N/sp3NH Hybrid Linear N4 Ligand Ph-BINAN-H-Py
    Nakatsuka, Hiroshi
    Yamamura, Tomoya
    Shuto, Yoshihiro
    Tanaka, Shinji
    Yoshimura, Masahiro
    Kitamura, Masato
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (25) : 8138 - 8149
  • [4] Ruthenium(II) carbonyl complexes of P,P and P,O donor diphosphine ligands, Ph2P(CH2)nPPh2 and Ph2P(CH2)nP(O)Ph2, n=2, 3 and their activities in catalytic transfer hydrogenation reactions
    Deb, Biswajit
    Dutta, Dipak Kumar
    JOURNAL OF COORDINATION CHEMISTRY, 2018, 71 (08) : 1205 - 1213
  • [5] New chiral ligand N-toluenesulfonyl-2,2′-dimethoxy-6,6′-diaminobiphenyl for catalytic asymmetric transfer hydrogenation of ketones
    Chen, YX
    Li, YM
    Lam, KH
    Chan, ASC
    CHINESE JOURNAL OF CHEMISTRY, 2002, 20 (06) : 606 - 609
  • [6] New Chiral Ligand N-Toluenesulfonyl-2,2′-dimethoxy-6,6′-diaminobiphenyl for Catalytic Asymmetric Transfer Hydrogenation of Ketones
    陈亿新
    李月明
    林剑虹
    陈新滋
    Chinese Journal of Chemistry, 2002, (06) : 606 - 609
  • [7] A new dinuclear ruthenium complex bridged by azide:: [Ru2Cl2(μ-1,3-N3)2(Me2SO)6]
    Bai, LX
    Han, W
    Wang, WZ
    Liu, X
    Yan, SP
    Liao, DZ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : M953 - M954
  • [8] STRUCTURE OF THE LITHIUM THIOCYANATE-TETRAMETHYLPROPYLENEDIAMINE COMPLEX DIMER, [LINCS.ME2N(CH2)3NME2]2, WITH ASYMMETRIC NCS-BRIDGE BONDING - A NEW BONDING MODE FOR THE THIOCYANATE LIGAND
    ARMSTRONG, DR
    KHANDELWAL, AH
    RAITHBY, PR
    SNAITH, R
    STALKE, D
    WRIGHT, DS
    INORGANIC CHEMISTRY, 1993, 32 (10) : 2132 - 2136
  • [9] CRYSTAL AND MOLECULAR-STRUCTURES OF THE 1ST TRANS-MACRO-ANSA MONOCYCLOPHOSPHAZENE MACROCYCLE, TRANS-N3P3CL4 [HN-(CH2)3-O-(CH2)6-O-(CH2)3-NH]
    ZANIN, B
    SOURNIES, F
    LABARRE, JF
    ENJALBERT, R
    GALY, J
    JOURNAL OF MOLECULAR STRUCTURE, 1990, 240 : 77 - 88
  • [10] Synthesis and characterisation of the hexanuclear ruthenium diphosphine clusters [Ru6C(CO)(15){mu-Ph(2)P(CH2)(n)PPh(2)}] (n=1-4); Crystal structures where n=1-3
    Adatia, T
    Conole, G
    Drake, SR
    Johnson, BFG
    Kessler, M
    Lewis, J
    McPartin, M
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (04): : 669 - 673