Intramolecular [2+2] Cycloadditions of α-Heteroatom Substituted γ,δ-Unsaturated Ketenes

被引：0
|
作者：
Liu, Tzi-Chi [1 ]
Lin, Zih-Hao [1 ]
Yoo, Woo-Jin [1 ,2 ]
机构：
[1] Natl Taiwan Univ, Dept Chem, 1,Sec 4,Roosevelt Rd, Taipei 10617, Taiwan
[2] Natl Taiwan Univ, Ctr Emerging Mat & Adv Devices, 1,Sec 4,Roosevelt Rd, Taipei 10617, Taiwan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 10期
关键词：
Cycloaddition; Ketene; Isosteres; Synthetic Methods;
D O I：
10.1002/ajoc.202400302
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An improved synthetic procedure for the intramolecular ketene [2+2] cycloaddition was developed for the preparation of 1-heteroatom-substituted bicyclo[2.1.1]hexan-5-ones. It was found that the use of the Mukaiyama reagent (2-chloro-N-methyl-pyridinium iodide) was key to efficiently generate the alpha-heteroatom substituted homoallyl ketene intermediate for the cycloaddition reaction. The synthetic utility of the resulting bicyclic ketone was demonstrated through the preparation of a saturated variant of vortioxetine. A reliable method for the synthesis of 1-heteroatom-substituted bicyclo[2.1.1]hexan-5-one has been developed through an intramolecular ketene [2+2] cycloaddition reaction. image
引用
收藏
页数：4
相关论文
共 50 条
  • [31] A theoretical study on the stereoconvergency of the intramolecular radical cation [2+2] cycloadditions of bis(styrenes)
    Guo, Chenchen
    Cui, Lijie
    Chen, Bozhen
    Yuan, Jianhua
    Tian, Zhiyuan
    RSC ADVANCES, 2012, 2 (26): : 9932 - 9937
  • [32] Highly efficient induction of chirality in intramolecular [2+2] cycloadditions between ketenimines and imines
    Cossío, FP
    Arrieta, A
    Lecea, B
    Alajarín, M
    Vidal, A
    Tovar, F
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3633 - 3643
  • [33] Revisit of the Dessy-White intramolecular acetylene-acetylene [2+2] cycloadditions
    Lee, Chung-Chieh
    Leung, Man-kit
    Lee, Gene-Hsiang
    Liu, Yi-Hung
    Peng, Shie-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22): : 8417 - 8423
  • [34] "Snapshots" of Intramolecular Electron Transfer in Redox Tag-Guided [2+2] Cycloadditions
    Okada, Yohei
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 1882 - 1886
  • [35] Synthetic and computational studies on intramolecular [2+2] sulfonyl isocyanate-olefin cycloadditions
    Freitag, D
    Drees, M
    Goutal, S
    Strassner, T
    Metz, P
    TETRAHEDRON, 2005, 61 (23) : 5615 - 5621
  • [36] Controllable [2+2] cycloadditions of 1,5-bisallenyl-substituted compounds
    Jiang, Xuefeng
    Cheng, Xin
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) : 8009 - 8013
  • [37] Enantioselective nucleophilic catalysis:: The synthesis of aza-β-lactams through [2+2] cycloadditions of ketenes with azo compounds
    Berlin, Jacob M.
    Fu, Gregory C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) : 7048 - 7050
  • [38] Lewis Acid-Promoted [2+2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis
    Guo, Renyu
    Brown, M. Kevin
    ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (16) : 2253 - 2264
  • [39] Formal [(2+2)+2] and [(2+2)+(2+2)] nonconjugated dienediyne cascade cycloadditions
    Wu, YT
    Linden, A
    Siegel, JS
    ORGANIC LETTERS, 2005, 7 (20) : 4353 - 4355
  • [40] PHOTOCHEMICAL [2+2] CYCLOADDITIONS OF ACEANTHRYLENE
    SINGLETON, S
    PLUMMER, BF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 6 - ORGN
12345