Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles

被引:41
|
作者
Coldham, I
Crapnell, KM
Moseley, JD
Rabot, R
机构
[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
[2] AstraZeneca Pharmaceut, Proc R&D Dept, Avlon Works, Bristol BS10 7ZE, Avon, England
关键词
D O I
10.1039/b104390k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldehyde 2-formyl-2-(pent-4-enyl)-1,3-dithiane 1, containing both alkene and aldehyde functional groups, is a good substrate for intramolecular dipolar cycloaddition reactions after condensation with various N-alkyl alpha -amino-esters. This paper reports the optimization, scope and stereoselectivity of this reaction to give octahydroindoles (2-azabicyclo[4.3.0]nonanes).
引用
收藏
页码:1758 / 1763
页数:6
相关论文
共 50 条
  • [1] AN APPROACH TO THE SYNTHESIS OF PALAUAMINE VIA INTRAMOLECULAR AZOMETHINE YLIDE CYCLOADDITION
    OVERMAN, LE
    TELLEW, JE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 286 - ORGN
  • [2] Intramolecular azomethine ylide cycloaddition approach to the hexacyclic bisguanidine (-)-palau'amine
    Overman, LE
    Tellew, JE
    Trenkle, WC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 261 - ORGN
  • [3] Intramolecular dipolar cycloaddition reactions of azomethine ylides
    Coldham, I
    Hufton, R
    CHEMICAL REVIEWS, 2005, 105 (07) : 2765 - 2809
  • [4] Solid-phase synthesis:: Intramolecular azomethine ylide cycloaddition (→proline) and carbanilide cyclization (→hydantoin) reactions
    Gong, YD
    Najdi, S
    Olmstead, MM
    Kurth, MJ
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09): : 3081 - 3086
  • [5] PHOTOINITIATED INTRAMOLECULAR YLIDE-ALKENE CYCLOADDITION REACTIONS
    DITTAMI, JP
    NIE, XY
    BUNTEL, CJ
    RIGATTI, S
    TETRAHEDRON LETTERS, 1990, 31 (27) : 3821 - 3824
  • [6] Asymmetric synthesis of polycyclic 3-fluoroalkylproline derivatives by intramolecular azomethine ylide cycloaddition
    Rabasa-Alcaniz, Fernando
    Hammerl, Daniel
    Sanchez-Merino, Anabet
    Tejero, Tomas
    Merino, Pedro
    Fustero, Santos
    del Pozo, Carlos
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (16) : 2916 - 2923
  • [7] Evaluating the impact of tether position on the intramolecular oxazolium salt/ azomethine ylide cycloaddition sequence
    Rourk, Seth
    Warner, Don
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [8] New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions
    Dogan, Ozdemir
    Koyuncu, Hasan
    Garner, Philip
    Bulut, Adnan
    Youngs, Wiley J.
    Panzner, Matthew
    ORGANIC LETTERS, 2006, 8 (21) : 4687 - 4690
  • [9] 1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide
    Santos, Hugo
    Distiller, Amy
    D'Souza, Asha M.
    Arnoux, Quentin
    White, Jonathan M.
    Meyer, Adam G.
    Ryan, John H.
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (06): : 705 - 712
  • [10] An attempt to construct the C/D ring system of parkacine by intramolecular cycloaddition of azomethine ylide and alkyne
    Zhang, Wenxuan
    Wang, Jiming
    Luo, Xihuan
    Meng, Xiangbao
    Li, Zhongjun
    TETRAHEDRON LETTERS, 2016, 57 (18) : 1981 - 1984