Modular Synthesis of Multi-substituted Cyclobutanones Enabled by Oxyallyl Cations

被引：0
|
作者：
Wang, Meng [1 ,2 ,3 ]
Wang, Zhonggui [1 ]
Lu, Ping [1 ]
机构：
[1] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, 220 Handan Lu, Shanghai 200433, Peoples R China
[2] Dana Farber Canc Inst, Dept Canc Biol, Boston, MA 02115 USA
[3] Harvard Med Sch, Dept Biol Chem & Mol Pharmacol, Boston, MA 02115 USA
来源：
CHINESE JOURNAL OF CHEMISTRY | 2024年 / 42卷 / 05期
基金：
中国国家自然科学基金;
关键词：
Diastereoselectivity; Modular synthesis; Nucleophilic substitution; Organohalides; Oxyallyl cation; Precision functionalization; Strained molecules; 1,2,3,4-Tetrasubstituted cyclobutanes; NATURAL-PRODUCTS; SUBSTITUTION; TRANSFORMATIONS; DERIVATIVES; CATALYSIS;
D O I：
10.1002/cjoc.202300525
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Stereoselective synthesis of multi-substituted cyclobutanes with different substituents is still a daunting challenge in organic synthesis. We report here a practical and facile approach to synthesizing all-trans 2,3,4-trisubstituted cyclobutanones from readily available dichlorocyclobutanones. The substitution reaction proceeds smoothly via oxyallyl cation intermediates under mild basic conditions. Further transformation to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes was also explored.
引用
收藏
页码：459 / 463
页数：5
相关论文
共 50 条
  • [21] Photoredox/Sulfide Dual Catalysis for Modular Synthesis of Multi-substituted Furan Rings via Catalytic Indirect Reductive Quenching
    Matsukuma, Kakeru
    Tayu, Masanori
    Ogino, Takumi
    Ohrui, Sayaka
    Noji, Masahiro
    Hayashi, Satoshi
    Saito, Nozomi
    Chemistry - An Asian Journal, 2025, 20 (05)
  • [22] Synthesis of Multi-Substituted Cyclobutanes and Alkylidenecyclobutanes by the Reaction of Cyclobutylmagnesium Carbenoids with Nucleophiles
    Satoh, Tsuyoshi
    Kasuya, Takashi
    Ishigaki, Masashi
    Inumaru, Mio
    Miyagawa, Toshifumi
    Nakaya, Nobuhito
    Sugiyama, Shimpei
    SYNTHESIS-STUTTGART, 2011, (03): : 397 - 408
  • [23] Synthesis of Multi-substituted Benzamide Derivatives under Microwave Irradiation Conditions
    Jia Runhong
    Peng Juhua
    Ma Ning
    Yan Shu
    Tu Shujiang
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (09) : 1869 - 1872
  • [24] A new class of multi-substituted oxazole derivatives: Synthesis and antimicrobial activity
    Reddy, A. Babul
    Hymavathi, R. V.
    Swamy, G. Narayana
    JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (03) : 495 - 509
  • [25] Synthesis, Bioactivity, Pharmacokinetic and Biomimetic Properties of Multi-Substituted Coumarin Derivatives
    Katopodi, Annita
    Tsotsou, Evangelia
    Iliou, Triantafylia
    Deligiannidou, Georgia-Eirini
    Pontiki, Eleni
    Kontogiorgis, Christos
    Tsopelas, Fotios
    Detsi, Anastasia
    MOLECULES, 2021, 26 (19):
  • [26] Synthesis of Multisubstituted Benzenes from Phenols via Multi-substituted Benzynes
    Nagai, Akira
    Kobayashi, Akihiro
    Sakata, Yuki
    Minami, Yasunori
    Uchida, Keisuke
    Hosoya, Takamitsu
    Yoshida, Suguru
    SYNTHESIS-STUTTGART, 2022, 54 (22): : 5017 - 5025
  • [27] Zirconium-Mediated Synthesis of Multi-substituted Dibenzosilole and Benzonaphthosilole Derivatives
    Qu H.
    Zhang X.
    Chen X.
    Zhang H.
    Men Y.
    Li J.
    Transactions of Tianjin University, 2018, 24 (6) : 538 - 546
  • [28] Zirconium-Mediated Synthesis of Multi-substituted Dibenzosilole and Benzonaphthosilole Derivatives
    Hongmei Qu
    Xin Zhang
    Xu Chen
    Hui Zhang
    Yican Men
    Junqiu Li
    Transactions of Tianjin University, 2018, 24 (06) : 538 - 546
  • [29] Diastereoselective reactions of chiral, nitrogen-substituted oxyallyl cations.
    Walters, MA
    Sponholtz, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 605 - ORGN
  • [30] Highly Selective Synthesis of Multi-substituted Olefins Mediated by Zirconocene Complexes
    Hyodo, Keita
    Nishihara, Yasushi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (08) : 792 - 802
12345