Enantioselective synthesis of six membered carbocycles through [4+2] cycloaddition reactions of chiral 2-amino-1,3-butadienes and tungsten vinyl Fischer type carbene complexes

被引：28
|
作者：
Barluenga, J
Aznar, F
Martin, A
Barluenga, S
机构：
[1] Inst. Univ. Quim. Orgmet. Enrique M., Universidad de Oviedo, 33071 Oviedo, C/ Julián Clavería S/N
来源：
TETRAHEDRON | 1997年 / 53卷 / 27期
关键词：
D O I：
10.1016/S0040-4020(97)00586-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Amino-1,3-butadienes 1 react with carbene complexes 2 to yield, after hydrolysis, cyclohexanone derivatives. The use of chiral enantiomerically pure dienes 19 allow the access to enantio-enriched cycloadduct complexes. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：9323 / 9340
页数：18
相关论文
共 50 条
  • [1] Enantioselective Synthesis of six Membered Carbocycles through [4+2] Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes and Tungsten Vinyl Fischer Type Carbene Complexes
    Barluenga, J.
    Aznar, F.
    Martin, A.
    Barluenga, S.
    Tetrahedron, 53 (27):
  • [2] STEREOSELECTIVE SYNTHESIS OF 7-MEMBERED CARBOCYCLES FROM 2-AMINO-1,3-BUTADIENES AND VINYL CHROMIUM FISCHER-TYPE CARBENES
    BARLUENGA, J
    AZNAR, F
    MARTIN, A
    VAZQUEZ, JT
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) : 9419 - 9426
  • [3] Stereoselective synthesis of seven-membered carbocycles from 2-amino-1,3-butadienes and vinyl chromium fischer-type carbenes
    Barluenga, J.
    Aznar, F.
    Martin, A.
    Vazquez, J.T.
    Journal of the American Chemical Society, 1995, 117 (37)
  • [4] Chiral heterosubstituted 1,3-butadienes:: Synthesis and [4+2] cycloaddition reactions
    Barluenga, J
    Suárez-Sobrino, A
    Lopez, LA
    ALDRICHIMICA ACTA, 1999, 32 (01) : 4 - 15
  • [5] 1ST [4+2] CYCLOADDITION REACTION BETWEEN VINYL FISCHER TYPE CARBENE COMPLEXES AND CHIRAL 2-AMINO-1,3-DIENES
    BARLUENGA, J
    AZNAR, F
    MARTIN, A
    BARLUENGA, S
    GARCIAGRANDA, S
    PANEQUEOUEVEDO, AA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) : 843 - 844
  • [6] Cycloaddition reactions of chiral 2-amino-1,3-butadienes with nitroalkenes: Synthesis of enantiomerically pure 4-nitrocyclohexanones
    Barluenga, J
    Aznar, F
    Ribas, C
    Valdes, C
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20): : 6746 - 6753
  • [7] Fischer Carbene Complexes in Heterocyclic Synthesis. Selective Cycloaddition Reactions to 2-Aza-1,3-butadienes
    J Org Chem, 26 (9229):
  • [8] Fischer carbene complexes in heterocyclic synthesis.: Selective cycloaddition reactions to 2-aza-1,3-butadienes
    Barluenga, J
    Tomás, M
    Ballesteros, A
    Santamaría, J
    Suárez-Sobrino, A
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26): : 9229 - 9235
  • [9] [4+2] CYCLOADDITION REACTIONS OF VARIOUS 1,3-DIAZA-1,3-BUTADIENES WITH KETENES
    MAZUMDAR, SN
    MAHAJAN, MP
    TETRAHEDRON, 1991, 47 (08) : 1473 - 1484
  • [10] Efficient synthesis of 2-alkoxy-1,3-butadienes by methylenation of alkenyl Fischer carbene complexes
    Barluenga, Jose
    Vicente, Ruben
    Lopez, Luis A.
    Tomas, Miguel
    ARKIVOC, 2007, : 356 - 363
12345