SYNTHESES OF FUNCTIONALIZED CYCLIC MOLECULES BY PALLADIUM-CATALYZED CYCLIZATION OF PROPARGYLIC ESTERS WITH BIS-NUCLEOPHILES

被引:25
作者
Yoshida, Masahiro [1 ]
机构
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
基金
日本学术振兴会;
关键词
Cyclization; Palladium Catalyst; Propargylic Compound; Nucleophile; RING EXPANSION REACTION; CARBONATES; DERIVATIVES; PHENOLS; CONSTRUCTION; CHEMISTRY; OXIRANES; 4-METHOXYCARBONYLOXY-2-BUTYN-1-OLS; SUBSTITUTION; METHODOLOGY;
D O I
10.3987/REV-13-776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is known that propargylic esters react with palladium complex leading to pi-propargylpalladium complexes, which further cause various transformations in the presence of soft nucleophiles to produce the corresponding products. Among them, palladium-catalyzed cyclization of propargylic esters with bis-nucleophiles is one of the useful methodologies for the construction of functionalized cyclic molecules in one step. Since the pioneering work reported by Tsuji in 1985, a considerable number of reactions have been reported by the use of various bis-nucleophiles. In this review, a comprehensive overview of the studies on palladium-catalyzed reactions of propargylic esters with bis-nucleophiles is described, in which various functionalized cyclic molecules can be synthesized in a regio- and stereoselective manner.
引用
收藏
页码:1835 / 1864
页数:30
相关论文
共 50 条
  • [41] Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones
    Bennett, Nathan B.
    Duquette, Douglas C.
    Kim, Jimin
    Liu, Wen-Bo
    Marziale, Alexander N.
    Behenna, Douglas C.
    Virgil, Scott C.
    Stoltz, Brian M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (14) : 4414 - 4418
  • [42] Palladium-Catalyzed Asymmetric Direct Intermolecular Allylation of α-Aryl Cyclic Vinylogous Esters: Divergent Synthesis of (+)-Oxomaritidine and (-)-Mesembrine
    Wang, Wei
    Dai, Jun
    Yang, Qiqiong
    Deng, Yu-Hua
    Peng, Fangzhi
    Shao, Zhihui
    ORGANIC LETTERS, 2021, 23 (03) : 920 - 924
  • [43] Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization
    Pan, Yuan-Yuan
    Wu, Ya-Nan
    Chen, Zhen-Zhen
    Hao, Wen-Juan
    Li, Guigen
    Tu, Shu-Jiang
    Jiang, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (11) : 5764 - 5770
  • [44] Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Vinyl Cyclopropanes and β,γ-Unsaturated α-Keto Esters: An Effective Route to Highly Functionalized Cyclopentanes
    Mei, Liang-yong
    Wei, Yin
    Xu, Qin
    Shi, Min
    ORGANOMETALLICS, 2012, 31 (21) : 7591 - 7599
  • [45] Palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with cyclobutanone oxime esters and DABSO
    Zhou, Nengneng
    Xu, Qiankun
    Xia, Ziqin
    Kuang, Kaimo
    Wu, Sixin
    Li, Wenping
    Zhang, Man
    CHEMICAL COMMUNICATIONS, 2022, 58 (14) : 2335 - 2338
  • [46] Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor
    Chang, Zhe
    Ma, Tong
    Zhang, Yu
    Dong, Zheng
    Zhao, Heng
    Zhao, Depeng
    MOLECULES, 2020, 25 (05):
  • [47] Facile synthesis of HFIP esters-containing 2H-benzopyrans H-benzopyrans through palladium-catalyzed one-pot cyclization/carbonylation using formic acid as the CO source
    Wen, Dan
    Yao, Boyu
    Qi, Xinxin
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2024, 436
  • [48] Bismuth(iii)-catalyzed bis-cyclization of propargylic diol-esters: a unified approach for the synthesis of [5,5]- and [6,5]-oxaspirolactones
    Kambale, Digambar A.
    Borade, Balasaheb R.
    Kontham, Ravindar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (30) : 6618 - 6622
  • [49] Palladium-Catalyzed Ring Opening of Cyclopropane-Appended Spirotricyclic Olefins with Soft Nucleophiles and Organoboronic Acids: Facile Synthesis of Functionalized Spiro[2.4]heptenes
    Jijy, Eliyan
    Prakash, Praveen
    Baiju, Thekke Veettil
    Shimi, Machery
    Yamamoto, Yoshinori
    Suresh, Eringathodi
    Radhakrishnan, Kokkuvayil Vasu
    SYNTHESIS-STUTTGART, 2014, 46 (19): : 2629 - 2643
  • [50] Palladium-Catalyzed Three-Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis-Fused Bicyclo[4.3.0]nonenes
    Shu, Wei
    Jia, Guochen
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) : 2788 - 2791