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
  • [21] Synthesis and photochemistry of β-(3-substituted-2-furyl)-o-divinylbenzenes;: [2+2] and [4+2] intramolecular cycloadditions
    Skoric, I
    Hutinec, A
    Marinic, Z
    Sindler-Kulyk, M
    ARKIVOC, 2003, : 87 - 97
  • [22] Mechanism and Regioselectivity of Intramolecular [2+2] Cycloaddition of Ene-Ketenes: A DFT Study
    Fan, Xing
    Zhang, Pan
    Wang, Yi
    Yu, Zhi-Xiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (37) : 5985 - 5994
  • [23] Chirality transfer intramolecular [2+2] cycloadditions of electron deficient allenes and alkenes
    Xu, Yao
    Brown, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [24] A CYCLOBUTANE-FUNGICIDE VIA INTERMOLECULAR AND INTRAMOLECULAR PHOTOCHEMICAL [2+2]-CYCLOADDITIONS
    BUHLER, N
    BELLUS, D
    CHIMIA, 1981, 35 (07) : 254 - 254
  • [25] Thermal [2+2] intramolecular cycloadditions of fuller-1,6-enynes
    Martín, N
    Altable, M
    Filippone, S
    Martín-Domenech, A
    Güell, M
    Solà, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) : 1439 - 1442
  • [26] Ruthenium-catalyzed [2+2] cycloadditions of 2-substituted norbornenes
    Jordan, RW
    Tam, W
    ORGANIC LETTERS, 2000, 2 (19) : 3031 - 3034
  • [27] SYNTHESIS OF BIOLOGICALLY-ACTIVE SMALL CARBOCYCLIC RINGS VIA [2+2]-CYCLOADDITIONS OF HETEROSUBSTITUTED KETENES
    BELLUS, D
    MARTIN, P
    GREUTER, H
    STEINER, E
    CHIMIA, 1980, 34 (05) : 237 - 238
  • [28] INTRAMOLECULAR [2+2]-CYCLOADDITIONS OF 2,2'-BIS(1-ARYLVINYL)-SUBSTITUTED BIPHENYLS INDUCED BY PHOTO-ELECTRON TRANSFER
    SADLEK, O
    GOLLNICK, K
    POLBORN, K
    GRIESBECK, AG
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (22) : 2300 - 2301
  • [29] Regioselectivity and Reactivity of Intramolecular [2+2] Cycloaddition Reactions of Acyl Ketenes: Experimental and Theoretical Studies
    Zahedifar, Mahboobeh
    Sheibani, Hassan
    Saheb, Vahid
    SYNLETT, 2018, 29 (14) : 1836 - 1841
  • [30] A Catalyst and Base Free Approach to Polycyclic Aromatic Compounds via Intramolecular [2+2] and retro-[2+2] Cycloadditions
    Lu, Aoyun
    Li, Tao
    Wang, Jiayi
    Song, Gonghua
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (07) : 1773 - 1777
12345