Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis

被引:21
|
作者
Kohn, Benjamin L. [1 ]
Jarvo, Elizabeth R. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
ENANTIOSELECTIVE SYNTHESIS; NEUTRAL CONDITIONS; 3+2 CYCLOADDITION; COUPLING REACTION; COMPLEXES; ALLYLATION; PROPARGYL; CASCADE; ALLENES; ALDEHYDES;
D O I
10.1021/ol2019423
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.
引用
收藏
页码:4858 / 4861
页数:4
相关论文
共 50 条
  • [1] Palladium-catalyzed diastereoselective synthesis of isoindolinones
    Cho, CS
    Chu, DY
    Lee, DY
    Shim, SC
    Kim, TJ
    Lim, WT
    Heo, NH
    SYNTHETIC COMMUNICATIONS, 1997, 27 (23) : 4141 - 4158
  • [2] Palladium-catalyzed annulation
    Larock, RC
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 111 - 124
  • [3] Palladium-catalyzed annulation
    Larock, RC
    PURE AND APPLIED CHEMISTRY, 1999, 71 (08) : 1435 - 1442
  • [4] A Palladium-Catalyzed Formal (4+1) Annulation: A New Approach to Cyclopentene Construction
    Widenhoefer, Ross A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) : 6950 - 6952
  • [5] Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine
    Yeh, Li-Hsuan
    Wang, Hung-Kai
    Pallikonda, Gangaram
    Ciou, Yu-Lun
    Hsieh, Jen-Chieh
    ORGANIC LETTERS, 2019, 21 (06) : 1730 - 1734
  • [6] PALLADIUM-CATALYZED ANNULATION REACTIONS OF 1,8-DIIODONAPHTHALENE
    DYKER, G
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01): : 234 - 238
  • [7] Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products
    Horino, Yoshikazu
    Sugata, Miki
    Sugita, Tetsu
    Aimono, Ataru
    Abe, Hitoshi
    TETRAHEDRON LETTERS, 2017, 58 (22) : 2131 - 2134
  • [8] Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions
    Yip, Kai-Tai
    Zhu, Nian-Yong
    Yang, Dan
    ORGANIC LETTERS, 2009, 11 (09) : 1911 - 1914
  • [9] Palladium-catalyzed annulation of monosubstituted β-diketones
    Buono, F
    Tenaglia, A
    SYNLETT, 1998, (10) : 1153 - +
  • [10] Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes
    Huang, QH
    Larock, RC
    ORGANIC LETTERS, 2002, 4 (15) : 2505 - 2508