Regiodivergent Synthesis of Functionalized Indene Derivatives via Pt-Catalyzed Rautenstrauch Reaction of Propargyl Carbonates

被引:56
作者
Zhao, Jinbo [1 ]
Clark, Daniel A. [1 ]
机构
[1] Syracuse Univ, Dept Chem, Ctr Sci & Technol 1 014, Syracuse, NY 13244 USA
关键词
ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALKYLATION REACTIONS; SUBSTITUTED INDENES; EFFICIENT FORMATION; INDANONES; CYCLIZATION; COMPLEXES; CYCLOISOMERIZATION; PLATINUM;
D O I
10.1021/ol300158d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regiodivergent synthesis of functionalized indene derivatives from a Pt-catalyzed Rautenstrauch reaction of propargyl carbonate is described. A one-pot Rautenstrauch/Tsuji-Trost reaction delivering 2-indanones was realized efficiently using this methodology.
引用
收藏
页码:1668 / 1671
页数:4
相关论文
共 50 条
  • [41] Synthesis of 2-Vinylindole-3-Acetic Acid Derivatives via Cyanide-Catalyzed Imino-Stetter Reaction
    Seo, Hong-Ahn
    Cheon, Cheol-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17) : 7917 - 7923
  • [42] Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction
    Yang, Xiao-Chao
    Xu, Meng
    Wang, Jin-Bao
    Liu, Meng-Meng
    Mathey, Francois
    Hua, Yuan-Zhao
    Wang, Min-Can
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (20) : 3917 - 3926
  • [43] Synthesis of Tricyclic Isoquinoline Derivatives via Palladium-Catalyzed Tandem Reactions of 2,7-Alkadiynylic Carbonates with 2,3-Allenyl Sulfamides
    Huang, Xin
    Wu, Wangteng
    Song, Shihua
    Fu, Chunling
    Ma, Shengming
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2791 - 2805
  • [44] Synthesis of C3-functionalized indole derivatives via Bronsted acid-catalyzed regioselective arylation of 2-indolylmethanols with guaiazulene
    Liu, Yang
    Cao, Meng
    Zhang, Shangxi
    Wang, Zhenxi
    Dai, Xin
    Jiang, Xinde
    Dong, Yucheng
    Fu, Jie
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1510 - 1517
  • [45] N-Heterocyclic carbene-catalyzed synthesis of functionalized 3-hydroxypyrrolidinones via a domino aza-Michael/aldol reaction
    Zhu, Yan-fang
    Cai, Chun
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) : 5104 - 5107
  • [46] Unexpected Pd-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Alder-Ene Reaction: Facile Synthesis of Some Not Readily Available 2,3-Dihydrofuran Derivatives
    Shen, Ruwei
    Zhu, Shugao
    Huang, Xian
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) : 4118 - 4123
  • [47] A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction
    Gassa, Federico
    Contini, Alessandro
    Fontana, Gabriele
    Pellegrino, Sara
    Gelmi, Maria Luisa
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) : 7099 - 7106
  • [48] Lewis acid-catalyzed synthesis of silafluorene derivatives from biphenyls and dihydrosilanes via a double sila-Friedel-Crafts reaction
    Dong, Yafang
    Takata, Yuta
    Yoshigoe, Yusuke
    Sekine, Kohei
    Kuninobu, Yoichiro
    CHEMICAL COMMUNICATIONS, 2019, 55 (88) : 13303 - 13306
  • [49] New method for the synthesis of functionalized 1,3-bis-exocyclic dienes via a palladium-catalyzed reaction. Scope and synthetic applications
    Lomberget, T
    Bouyssi, D
    Balme, G
    SYNTHESIS-STUTTGART, 2005, (02): : 311 - 329
  • [50] Synthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction
    Saleh, Nidal
    Voituriez, Arnaud
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10) : 4371 - 4377