Novel carbonyl-dependent regioselective allylation via diethylzinc-mediated umpolung of π-allylpalladium

被引:24
作者
Kimura, M [1 ]
Ogawa, Y [1 ]
Shimizu, M [1 ]
Sueishi, M [1 ]
Tanaka, S [1 ]
Tamaru, Y [1 ]
机构
[1] Nagasaki Univ, Fac Engn, Dept Appl Chem, Nagasaki 8528521, Japan
关键词
D O I
10.1016/S0040-4039(98)01448-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed allylation of carbonyls (1.1 - 1.5 mmol) with allylic esters 3a-d (1 mmol) in the presence of Pd(PPh3)(4) (0.05 mmol) and Et2Zn (2.4 mmol) in THF at room temperature shows marked carbonyl-dependent regioselectivity, providing alpha-allylation products 5 with benzaldehyde and gamma-allylation products 6 with acetone and ethyl acetate. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6903 / 6906
页数:4
相关论文
共 8 条
  • [1] HOPPE D, 1986, ANGEW CHEM, V98, P171
  • [2] REAGENT-CONTROLLED ENANTIOSELECTIVE HOMOALDOL REACTION WITH CHIRAL 1-OXYALLYLLITHIUM DERIVATIVES - ENANTIO-DIVERGENT TUNING BY ACHIRAL TITANIUM REAGENTS
    KRAMER, T
    HOPPE, D
    [J]. TETRAHEDRON LETTERS, 1987, 28 (43) : 5149 - 5152
  • [3] Unique regio- and stereoselectivity in the allylation of benzaldehyde with 2-substituted allylzincs generated by umpolung of π-allylpalladium
    Shimizu, M
    Kimura, M
    Tanaka, S
    Tamaru, Y
    [J]. TETRAHEDRON LETTERS, 1998, 39 (07) : 609 - 612
  • [4] Streitwieser A., 1992, INTRO ORGANIC CHEM
  • [6] HIGHLY STEREOSELECTIVE ALLYLATION OF BENZALDEHYDE - GENERATION OF A STEREOCHEMICALLY DEFINED ALLYLZINC SPECIES FROM A PI-ALLYLPALLADIUM INTERMEDIATE AND DIETHYLZINC
    TAMARU, Y
    TANAKA, A
    YASUI, K
    GOTO, S
    TANAKA, S
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 787 - 789
  • [7] PALLADIUM-MEDIATED INTRAMOLECULAR C-N BOND FORMATION BETWEEN TERTIARY-AMINES AND ALKENES
    VANDERSCHAAF, PA
    SUTTER, JP
    GRELLIER, M
    VANMIER, GPM
    SPEK, AL
    VANKOTEN, G
    PFEFFER, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) : 5134 - 5144
  • [8] USE OF PI-ALLYLPALLADIUM AS A NUCLEOPHILE VIA AN ALKYL-ALLYL EXCHANGE-REACTION WITH ALKYLZINC
    YASUI, K
    GOTO, Y
    YAJIMA, T
    TANISEKI, Y
    FUGAMI, K
    TANAKA, A
    TAMARU, Y
    [J]. TETRAHEDRON LETTERS, 1993, 34 (47) : 7619 - 7622