Nickel-catalyzed reductive cyclization of unactivated 1,6-enynes in the presence of organozinc reagents

被引：47
作者：
Chen, Mao [1 ]
Weng, Yue [1 ]
Guo, Mian [1 ]
Zhang, Hua [1 ]
Lei, Aiwen [1 ]
机构：
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 12期
关键词：
cyclization; enynes; nickel; organozinc reagents; synthetic methods;
D O I：
10.1002/anie.200704452
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Pyrrolidine and tetrahydrofuran derivatives were synthesized in a highly stereoselective manner through the Ni-catalyzed reduction of the title compounds under mild conditions (see scheme). The product of cyclization is initially associated with both a Ni and a Zn species, the removal of which by elimination and hydrolysis corresponds to the formal incorporation of dihydrogen. acac=acetylacetonate; R=alkyl, aryl; X=N, O. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：2279 / 2282
页数：4
相关论文
共 55 条
  • [1] The behavior of 1,n-enynes in the presence of transition metals
    Aubert, C
    Buisine, O
    Malacria, M
    [J]. CHEMICAL REVIEWS, 2002, 102 (03) : 813 - 834
  • [2] Rh-catalyzed enyne cycloisomerization
    Cao, P
    Wang, B
    Zhang, XM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6490 - 6491
  • [3] The asymmetric intramolecular Heck reaction in natural product total synthesis
    Dounay, AB
    Overman, LE
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2945 - 2963
  • [4] Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts
    Fairlamb, IJS
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1048 - 1052
  • [5] NICKEL EFFECT
    FISCHER, K
    JONAS, K
    MISBACH, P
    STABBA, R
    WILKE, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1973, 12 (12): : 943 - 953
  • [6] FISCHER K, 1973, ANGEW CHEM, V85, P1001
  • [7] Cyclopentenones from carbonylative cycloaddition of Mackenzie's allyl nickel complexes and acetylenes
    García-Gómez, G
    Moretó, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 878 - 879
  • [8] Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
  • [9] 2-O
  • [10] GEIS O, 1998, ANGEW CHEM, V110, P955, DOI DOI 10.1002/(SICI)1521-3757(19980403)110:7955::AID-9
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