Enol tosylates as viable partners in Pd-catalyzed cross-coupling reactions

被引:64
作者
Steinhuebel, D [1 ]
Baxter, JM [1 ]
Palucki, M [1 ]
Davies, IW [1 ]
机构
[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1021/jo051590s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we demonstrate functionalized enol tosylates to be robust substrates that undergo Suzuki-Miyaura, Sonogashira, and Stille cross-coupling reactions to provide stereodefined trisubstituted unsaturated esters.
引用
收藏
页码:10124 / 10127
页数:4
相关论文
共 21 条
  • [1] PALLADIUM-CATALYZED COUPLING OF ARYL ARENESULFONATES WITH ORGANOSTANNANES
    BADONE, D
    CECCHI, R
    GUZZI, U
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6321 - 6323
  • [2] Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones
    Batey, RA
    Thadani, AN
    Smil, DV
    [J]. ORGANIC LETTERS, 1999, 1 (10) : 1683 - 1686
  • [3] Stereoselective enol tosylation:: Preparation of trisubstituted α,β-unsaturated esters
    Baxter, JM
    Steinhuebel, D
    Palucki, M
    Davies, IW
    [J]. ORGANIC LETTERS, 2005, 7 (02) : 215 - 218
  • [4] Furan forming reactions of cis-2-alken-4-yn-1-ones
    Casey, CP
    Strotman, NA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) : 2576 - 2581
  • [5] Design and implementation of new, silicon-based, cross-coupling reactions: Importance of silicon-oxygen bonds
    Denmark, SE
    Sweis, RF
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) : 835 - 846
  • [6] Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates
    Denmark, SE
    Sweis, RF
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3771 - 3774
  • [7] First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction
    Fu, XY
    Zhang, SY
    Yin, JG
    McAllister, TL
    Jiang, SA
    Tann, CH
    Thiruvengadam, TK
    Zhang, FC
    [J]. TETRAHEDRON LETTERS, 2002, 43 (04) : 573 - 576
  • [8] Gebauer O, 2000, SYNTHESIS-STUTTGART, P588
  • [9] Practical synthesis of (Z)-polyaromatic and heteroaromatic vinylacetylenes
    Hayford, A
    Kaloko, J
    El-Kazaz, S
    Bass, G
    Harrison, C
    Corprew, T
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2671 - 2673
  • [10] Huffman MA, 1999, SYNLETT, P471