Chiral 2,2′-bipyridines, 5,6-dihydro-1,10-phenanthrolines and 1,10-phenanthrolines as ligands for enantioselective palladium catalyzed allylic substitution

被引：39
|
作者：
Chelucci, G [1 ]
Saba, A [1 ]
Sanna, G [1 ]
Soccolini, F [1 ]
机构：
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 16期
关键词：
D O I：
10.1016/S0957-4166(00)00296-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A number of chiral 5,6-dihydro-1,1-phenanthrolines, 5,6-dihydrobenzo[b]-1,1-phenanthrolines and 5,6,7,8-tetrahydro-2-quinolinylquinoline derived from (-)-pinocarvone were prepared and assessed in the enantioselective palladium catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl-malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the drastic reduction of the stereoselectivity of the reaction. Enantioselectivities up to 81% were obtained. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码：3427 / 3438
页数：12
相关论文
共 50 条
  • [31] Synthesis and properties of 3,3′-polymethylene-2,2′-bibenzo[b]-1,10-phenanthrolines
    Rahman, A. F. M. Motiur
    Jahng, Yurngdong
    HETEROCYCLES, 2008, 75 (04) : 871 - 877
  • [32] PEROXYDISULPHATE OXIDATION OF IRON(2) COMPLEXES OF SUBSTITUTED 1,10-PHENANTHROLINES AND RELATED COMPOUNDS
    BURGESS, J
    PRINCE, RH
    JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1966, (12): : 1772 - &
  • [33] Convenient synthesis of 5-aryl(alkyl)sulfanyl-1,10-phenanthrolines from 5,6-epoxy-5,6-dihydro-1,10-phenanthroline, and their activity towards fungal β-D-glycosidases
    Dotsenko, Irina A.
    Curtis, Matthew
    Samoshina, Nataliya M.
    Samoshin, Vyacheslav V.
    TETRAHEDRON, 2011, 67 (39) : 7470 - 7478
  • [34] Unique syndio-selectivity in CO/styrene copolymerization reaction catalyzed by palladium complexes with 2-(2′-oxazolinyl)-1,10-phenanthrolines
    Meduri, Angelo
    Cozzula, Daniela
    D'Amora, Angela
    Zangrando, Ennio
    Gladiali, Serafino
    Milani, Barbara
    DALTON TRANSACTIONS, 2012, 41 (25) : 7474 - 7484
  • [35] Imidazo[4,5-f]-1,10-phenanthrolines:: Versatile ligands for the design of metallomesogens
    Cardinaels, Thomas
    Ramaekers, Jan
    Nockemann, Peter
    Driesen, Kris
    Van Hecke, Kristof
    Van Meervelt, Luc
    Lei, Shengbin
    De Feyter, Steven
    Guillon, Daniel
    Donnio, Bertrand
    Binnemans, Koen
    CHEMISTRY OF MATERIALS, 2008, 20 (04) : 1278 - 1291
  • [36] SYNTHESES OF 2,9-BIS(HALOMETHYL)-1,10-PHENANTHROLINES - POTENTIAL ROBUST LIGANDS FOR METAL OXIDATION CATALYSTS
    BEER, RH
    JIMENEZ, J
    DRAGO, RS
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07): : 1746 - 1747
  • [37] A FRIEDLANDER APPROACH TO NOVEL 1,10-PHENANTHROLINES AND THEIR USE AS LIGANDS FOR RU(II) AND CU(I)
    HUNG, CY
    WANG, TL
    SHI, ZQ
    THUMMEL, RP
    TETRAHEDRON, 1994, 50 (36) : 10685 - 10692
  • [38] Synthesis and properties of 3,2′-polymethylene-2-phenylbenzo[b]-1,10-phenanthrolines
    Rahman, A. F. M. Motiur
    Jahng, Yurngdong
    HETEROCYCLES, 2007, 71 (09) : 2003 - 2010
  • [39] Concave reagents, 47.: Concave 1,10-phenanthrolines as tailored ligands for copper(I)-catalyzed diastereoselective cyclopropanations
    Lüning, U
    Fahrenkrug, F
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (04) : 916 - 923
  • [40] 2,4-Diaryl-5,6-dihydro-1,10-phenanthrolines with Furyl or Thienyl Moiety at 4-Position: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity
    Thapa, Pritam
    Lee, Eung-Seok
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (05): : 1769 - 1772
12345