A cationic palladium(II) complex-catalyzed Diels-Alder reaction

被引:42
作者
Oi, S [1 ]
Kashiwagi, K [1 ]
Inoue, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Engn, Dept Chem Mat, Sendai, Miyagi 9808579, Japan
关键词
D O I
10.1016/S0040-4039(98)01288-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cationic palladium(II) complex, [PdL2(RCN)(2)](BF4)(2) has been found to catalyze the Diels-Alder reaction of alpha, beta-unsaturated carbonyl compounds with dienes, affording the corresponding cycloadducts in good yields. Excellent enantioselectivity can be achieved in the reaction of N-acryloyloxazolidinone and cyclopentadiene by use of a chiral ligand, BINAP. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6253 / 6256
页数:4
相关论文
共 16 条
  • [1] Chiral ruthenium complexes as catalysts in enantioselective Diels-Alder reactions. Crystal structure of the Lewis acid dienophile adduct
    Carmona, D
    Cativiela, C
    Elipe, S
    Lahoz, FJ
    Lamata, MP
    Pilar, M
    de Viu, LR
    Oro, LA
    Vega, C
    Viguri, F
    [J]. CHEMICAL COMMUNICATIONS, 1997, (24) : 2351 - 2352
  • [2] Davenport AJ, 1997, CHEM COMMUN, P2347
  • [3] Chiral arene ruthenium complexes as asymmetric Diels-Alder catalysts
    Davies, DL
    Fawcett, J
    Garratt, SA
    Russell, DR
    [J]. CHEMICAL COMMUNICATIONS, 1997, (15) : 1351 - 1352
  • [4] HARD LIGANDS AS DONORS TO SOFT METALS .3. CATIONIC BIS(SOLVENT) COMPLEXES OF PALLADIUM(II) - CATIONS FOR CATALYSIS
    DAVIES, JA
    HARTLEY, FR
    MURRAY, SG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1980, (11): : 2246 - 2249
  • [5] BIS(IMINE)-COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACID CATALYSTS FOR THE DIELS-ALDER REACTION
    EVANS, DA
    LECTKA, T
    MILLER, SJ
    [J]. TETRAHEDRON LETTERS, 1993, 34 (44) : 7027 - 7030
  • [6] C-2-SYMMETRIC CATIONIC COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACIDS - COUNTERION EFFECTS IN THE ENANTIOSELECTIVE DIELS-ALDER REACTION
    EVANS, DA
    MURRY, JA
    VONMATT, P
    NORCROSS, RD
    MILLER, SJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 798 - 800
  • [7] BIS(OXAZOLINE)COPPER(II) COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE DIELS-ALDER REACTION
    EVANS, DA
    MILLER, SJ
    LECTKA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6460 - 6461
  • [8] USE OF ORGANOMETALLIC COMPLEXES OF RUTHENIUM IN THE LEWIS ACID-CATALYZED HETERO DIELS-ALDER REACTION
    FALLER, JW
    SMART, CJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (10) : 1189 - 1192
  • [9] HOMOGENEOUS CATALYSIS - [TI(CP-ASTERISK)2(H2O)2]2+ - AN AIR-STABLE, WATER-TOLERANT DIELS-ALDER CATALYST
    HOLLIS, TK
    ROBINSON, NP
    BOSNICH, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5464 - 5466
  • [10] The first highly enantioselective catalytic hetero-Diels-Alder reaction of ketones
    Johannsen, M
    Yao, S
    Jorgensen, KA
    [J]. CHEMICAL COMMUNICATIONS, 1997, (22) : 2169 - 2170