3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles

被引:11
作者
Okitsu, Takashi [1 ]
Kobayashi, Keiko [1 ]
Kan, Ryosuke [1 ]
Yoshida, Yuji [1 ]
Matsui, Yuki [1 ]
Wada, Akimori [1 ]
机构
[1] Kobe Pharmaceut Univ, Dept Organ Chem Life Sci, Higashinada Ku, 4-19-1 Motoyamakita Machi, Kobe, Hyogo 6588558, Japan
关键词
2+2 CYCLOADDITION REACTION; ORGANIC-SYNTHESIS; OXYALLYL CATIONS; ALLENAMIDES; RING; CYCLOPROPANES; AZETIDINES; ALKENES; DERIVATIVES; CLEAVAGE;
D O I
10.1021/acs.orglett.7b02194
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Methylene-4-amido-1,2-diazetidine (MADA) was prepared for the first time via formal [2 + 2] cycloaddition of an allenamide and an azodicarboxylate. MADA worked as a formal 1,4-dipole precursor toward nucleophilic addition with various silyl enol ethers and allyltrimethylsilanes.
引用
收藏
页码:4592 / 4595
页数:4
相关论文
共 34 条
  • [1] Synthesis and Functionalization of 3-Alkylidene-1,2-diazetidines Using Transition Metal Catalysis
    Brown, Michael J.
    Clarkson, Guy J.
    Inglis, Graham G.
    Shipman, Michael
    [J]. ORGANIC LETTERS, 2011, 13 (07) : 1686 - 1689
  • [2] Heterocycles from cyclopropanes: applications in natural product synthesis
    Carson, Cheryl A.
    Kerr, Michael A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3051 - 3060
  • [3] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [4] Azapeptide Synthesis Methods for Expanding Side-Chain Diversity for Biomedical Applications
    Chingle, Ramesh
    Proulx, Caroline
    Lubell, William D.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (07) : 1541 - 1556
  • [5] Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes
    de Nanteuil, F.
    De Simone, F.
    Frei, R.
    Benfatti, F.
    Serrano, E.
    Waser, J.
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (75) : 10912 - 10928
  • [6] Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition
    de Nanteuil, Florian
    Waser, Jerome
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (34) : 9009 - 9013
  • [7] Gold(I)-Catalyzed Intermolecular [2+2]Cycloadditions between Allenamides and Alkenes
    Faustino, Helio
    Bernal, Paloma
    Castedo, Luis
    Lopez, Fernando
    Mascarenas, Jose L.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (09) : 1658 - 1664
  • [8] FIRL J, 1969, TETRAHEDRON LETT, P1137
  • [9] REACTION OF AZIRIDINECARBOXYLIC ACIDS WITH THIOLS IN AQUEOUS-SOLUTION - THE FORMATION OF BETA-AMINO ACID
    HATA, Y
    WATANABE, M
    [J]. TETRAHEDRON, 1987, 43 (17) : 3881 - 3888
  • [10] Synthesis of 1-Alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening toward Diverse α-(Trifluoromethyl)Amines via Intermediate Azetidinium Salts
    Kenis, Sara
    D'hooghe, Matthias
    Verniest, Guido
    Tuyet Anh Dang Thi
    Chinh Pham The
    Tuyen Van Nguyen
    De Kimpe, Norbert
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (14) : 5982 - 5992