Acetylenes in catalysis: Enantioselective additions to carbonyl groups and imines and applications beyond

被引:290
作者
Cozzi, PG
Hilgraf, R
Zimmermann, N
机构
[1] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[2] Celgene, San Diego, CA 92121 USA
[3] Vertex Pharmaceut Inc, San Diego, CA 92121 USA
关键词
acetylenes; enantioselectivity; catalysis; metal complexes;
D O I
10.1002/ejoc.200400246
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acetylenes represent a class of versatile building blocks, which are widely used in organic synthesis. Over the past years, a considerable number of publications have appeared that focus on the enantioselective addition of acetylenes to carbonyls and imines. In addition, novel applications for acetylenes have emerged in the literature. We herein present an overview of recent results in these areas. (C) Wiley-VCH Verlag GmbH Co.
引用
收藏
页码:4095 / 4105
页数:11
相关论文
共 167 条
  • [1] Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B
    Amador, M
    Ariza, X
    Garcia, J
    Ortiz, J
    [J]. TETRAHEDRON LETTERS, 2002, 43 (15) : 2691 - 2694
  • [2] [Anonymous], J AM CHEM SOC
  • [3] [Anonymous], ANGEW CHEM
  • [4] Alkoxide-catalyzed addition of terminal alkynes to ketones
    Babler, JH
    Liptak, VP
    Phan, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 416 - 417
  • [5] Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species
    Balsells, J
    Davis, TJ
    Carroll, P
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10336 - 10348
  • [6] beta-silyl diorganozinc compounds - A new class of useful zinc reagents
    Berger, S
    Langer, F
    Lutz, C
    Knochel, P
    Mobley, TA
    Reddy, CK
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1496 - 1498
  • [7] BERGER S, 1997, ANGEW CHEM, V109, P1605
  • [8] Evidence for the in situ formation of copper acetylides during Pd/Cu catalyzed synthesis of enynes:: a new synthesis of allenynols
    Bertus, P
    Fécourt, F
    Bauder, C
    Pale, P
    [J]. NEW JOURNAL OF CHEMISTRY, 2004, 28 (01) : 12 - 14
  • [9] Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides
    Black, DA
    Arndtsen, BA
    [J]. ORGANIC LETTERS, 2004, 6 (07) : 1107 - 1110
  • [10] BLACK DA, 2004, ORG LETT