1-Aminovinylphosphonate Esters as Substrates for the Diels-Alder Reaction: First Synthetic and Theoretical Study

被引：3
作者：
Mercedes Jimenez-Andreu, M. [1 ]
Bueno-Moron, Jorge [1 ]
Sayago, Francisco J. [1 ]
Cativiela, Carlos [1 ]
Tejero, Tomas [1 ]
Merino, Pedro [2 ]
机构：
[1] Univ Zaragoza, CSIC, ISQCH, Dept Quim Organ, E-50009 Zaragoza, Spain
[2] Univ Zaragoza, Inst Biocomputac & Fis Sistemas Complejos BIFI, E-50009 Zaragoza, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 06期
关键词：
Cycloaddition; Olefination; Phosphorous compounds; Density functional calculations; Strained molecules; ANION-BINDING CATALYSIS; ALPHA-AMINO-ACID; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; STEREOSELECTIVE-SYNTHESIS; METAL-FREE; 1,3-DIPOLAR CYCLOADDITION; N-TOSYLHYDRAZONES; RECENT PROGRESS; DERIVATIVES; ROUTE;
D O I：
10.1002/ejoc.201801633
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Diels-Alder reaction of 1-aminovinylphosphonate esters has been studied for the first time as a suitable procedure leading to quaternary carbocyclic alpha-aminophosphonates. The reaction is influenced by steric effects at the phosphonate functionality (bulky groups hinder the reaction) and electronic effects at the amino group (electron-withdrawing substituents increase the reaction rate). The exo/endo ratio is constant, and no influence of the solvent is observed. The experimental results have been rationalized by DFT methods.
引用
收藏
页码：1268 / 1272
页数：5
相关论文
共 51 条
  • [1] From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis
    Adler, Pauline
    Fadel, Antoine
    Prunet, Joelle
    Rabasso, Nicolas
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (02) : 387 - 395
  • [2] Strategies for the synthesis of α- and β-amino vinylphosphonate
    Adler, Pauline
    Fadel, Antoine
    Rabasso, Nicolas
    [J]. TETRAHEDRON, 2014, 70 (30) : 4437 - 4456
  • [3] Advances in the synthesis of α-quaternary α-ethynyl α-amino acids
    Boibessot, Thibaut
    Benimelis, David
    Meffre, Patrick
    Benfodda, Zohra
    [J]. AMINO ACIDS, 2016, 48 (09) : 2081 - 2101
  • [4] Synthesis and biological analysis of novel glycoside derivatives of L-AEP, as targeted antibacterial agents
    Bovill, Richard
    Evans, Philip G.
    Howse, Gemma L.
    Osborn, Helen M. I.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (15) : 3774 - 3779
  • [5] DIELS-ALDER REACTIONS OF METHYL-N-ACYL-ALPHA,BETA-DEHYDROALANINATES WITH CYCLOPENTADIENE
    BUENO, MP
    CATIVIELA, C
    FINOL, C
    MAYORAL, JA
    JAIME, C
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (09): : 2182 - 2186
  • [6] Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids
    Cativiela, Carlos
    Diaz-de-Villegas, Maria D.
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (05) : 569 - 623
  • [7] Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids
    Cativiela, Carlos
    Ordonez, Mario
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (01) : 1 - 63
  • [8] Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine
    Cernak, Timothy A.
    Gleason, James L.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) : 102 - 110
  • [9] Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles
    Chintalapudi, V.
    Galvin, E. A.
    Greenaway, R. L.
    Anderson, E. A.
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (04) : 693 - 696
  • [10] Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates
    Choudhury, Abhijnan Ray
    Mukherjee, Santanu
    [J]. CHEMICAL SCIENCE, 2016, 7 (12) : 6940 - 6945
123456