Metal-Free and Diastereoselective Synthesis of 4-Oxa-δ-Lactams with 2-Aza-3-Silyloxy-1,3-Butadienes and Fluoroalkyl Acylsilanes

被引：0
|
作者：
Song, Dalu [1 ]
Zhang, Yunxiao [1 ]
He, Xiaoqian [1 ]
Zhou, Gang [1 ]
Zhang, Weilu [1 ]
Shen, Xiao [1 ,2 ,3 ]
机构：
[1] Wuhan Univ, Inst Adv Studies, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Fluorine & Nitrogen Chem & Adv Mat, Shanghai 200032, Peoples R China
[3] Wuhan Univ, Shenzhen Res Inst, Shenzhen 518057, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 28卷 / 11期
基金：
国家重点研发计划;
关键词：
Fluoroalkylation; 4-Oxo-delta-lactam; Hetero Diels-Alder reaction; Metal-free; Acylsilane; DIELS-ALDER REACTION; BRASSARD DIENE; ALDEHYDES; ACCESS;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report a diastereoselective [4+2] cycloaddition reaction of 2-aza-3-silyloxy-1,3-butadienes and fluoroalkyl acylsilanes for the synthesis of fluoroalkyl 4-oxa-delta-lactams without a metal catalyst or an additive under open-to-air conditions. The reaction features mild conditions, high efficiency and excellent diastereoselectivity, exhibiting a broad substrate scope and good functional group tolerance.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones
    Shkoor, Mohanad
    Riahi, Abdolmajid
    Fatunsin, Olumide
    Hussain, Ibrar
    Yawer, Mirza A.
    Lubbe, Mathias
    Reim, Stefanie
    Reinke, Helmut
    Fischer, Christine
    Langer, Peter
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (10) : 2182 - 2186
  • [32] Diastereoselective synthesis of spiro-[cyclopropane-1,3′-indolin]-2′-ones through metal-free cyclopropanation using tosylhydrazone salts
    Kapure, Jeevak Sopanrao
    Reddy, Chada Narsimha
    Adiyala, Praveen Reddy
    Nayak, Ranjita
    Nayak, V. Lakshma
    Nanubolu, Jagadeesh Babu
    Singarapu, Kiran Kumar
    Maurya, Ram Awatar
    RSC ADVANCES, 2014, 4 (72): : 38425 - 38432
  • [33] Chelation-control in the formal [3+3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One-pot synthesis of 3-aryl-3,4-dihydroisocoumarins
    Ullah, Ihsan
    Sher, Muhammad
    Khera, Rasheed Ahmad
    Ali, Asad
    Ibad, Muhammad Farooq
    Villinger, Alexander
    Fischer, Christine
    Langer, Peter
    TETRAHEDRON, 2010, 66 (10) : 1874 - 1884
  • [34] Diversity-Oriented Synthesis of Functionalized Phenols by Regioselective [3+3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with 3-Alkoxy-2-en-1-ones and Related Substrates
    Karapetyan, Gnuni
    Dang, Tuan T.
    Sher, Muhammad
    Ghochikyan, Tariel V.
    Saghyan, Ashot
    Langer, Peter
    CURRENT ORGANIC CHEMISTRY, 2012, 16 (05) : 557 - 565
  • [35] 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes:: synthesis and Diels-Alder reactivity
    Caballero, E
    Alonso, D
    Peláez, R
    Alvarez, C
    Puebla, P
    Sanz, F
    Medarde, M
    Tomé, F
    TETRAHEDRON LETTERS, 2004, 45 (08) : 1631 - 1634
  • [36] Ring opening of [1,2,3]triazolo[1,5-a]pyrazinium salts: Synthesis and some transformations of a novel type of 2-aza-1,3-butadienes
    Beres, M
    Hajos, G
    Riedl, Z
    Timari, G
    Messmer, A
    Holly, S
    Schantl, JG
    TETRAHEDRON, 1997, 53 (27) : 9393 - 9400
  • [37] Ring Opening of [1,2,3]Triazolo[1,5-a]pyrazinium Salts: Synthesis and Some Transformations of a Novel Type of 2-Aza-1,3-butadienes
    Beres, M.
    Hajos, G.
    Riedl, Z.
    Timari, G.
    Tetrahedron, 53 (27):
  • [38] Metal-Free Synthesis of 2-(per)Fluoroalkyl-3-nitro Indoles via Intramolecular Cyclization of Amides
    Sterligov, Grigorii K.
    Rasskazova, Maria A.
    Drokin, Egor A.
    Isaeva, Dilshodakhon K.
    Ageshina, Alexandra A.
    Rzhevskiy, Sergey A.
    Shurupova, Olga V.
    Topchiy, Maxim A.
    Minaeva, Lidiya I.
    Asachenko, Andrey F.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (19): : 14028 - 14037
  • [39] [4+2] Cycloadditions of 3-Tetrazolyl-1,2-diaza-1,3-butadienes: Synthesis of 3-Tetrazolyl-1,4,5,6-tetrahydropyridazines
    Lopes, Susana M. M.
    Brigas, Amadeu F.
    Palacios, Francisco
    Lemos, Americo
    Pinho e Melo, Teresa M. V. D.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (11) : 2152 - 2160
  • [40] Synthesis of 2,5-bis-arylpyridines by [4+2] cycloaddition of 1,4-bis aryl-2-aza-1,3-butadienes with electron-poor dienophiles
    Paparin, JL
    Crévisy, C
    Grée, R
    Toupet, L
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) : 411 - 418
12345