Chemodiscrimination of Olefin Bonds Through Cross-Metathesis Reactions - Synthesis of Functionalized β-Lactam and β-Amino Acid Derivatives

被引：10
|
作者：
Nonn, Melinda [1 ,2 ,3 ]
Benke, Zsanett [1 ,3 ]
Fustero, Santos [4 ]
Fulop, Ferenc [1 ,2 ,3 ]
Kiss, Lorand [1 ,3 ]
机构：
[1] Univ Szeged, Inst Pharmaceut Chem, Eotvos U 6, H-6720 Szeged, Hungary
[2] Hungarian Acad Sci, MTA SZTE Stereochem Res Grp, Eotvos U 6, H-6720 Szeged, Hungary
[3] Univ Szeged, Interdisciplinary Excellence Ctr, Inst Pharmaceut Chem, Szeged, Hungary
[4] Univ Valencia, Fac Farm, Dept Quim Organ, Av Vicente Andres Estelles S-N, E-46100 Valencia, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 31-32期
关键词：
Metathesis; Chemoselectivity; Amino acids; Lactams; Stereocontrol; STEREOSELECTIVE-SYNTHESIS; BUILDING-BLOCKS; FOLDAMERS; CYCLOADDITION; CONSTRUCTION; SELECTIVITY; AZETIDINES; CHEMICALS; PEPTIDES;
D O I：
10.1002/ejoc.201900101
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chemodifferentiation of C=C bonds of various diolefinated beta-lactams or beta-amino esters has been investigated through cross-metathesis reactions. The transformations involved substrate-dependent cross-metathesis of dialkenylated azetidinones, derived from the ring opening of constrained unsaturated bicyclic beta-lactam isomers. Cross-metathesis reactions have been carried out under various conditions and catalysts in view of chemodiscrimination affording functionalized beta-lactams or beta-amino acid derivatives.
引用
收藏
页码：5285 / 5293
页数：9
相关论文
共 50 条
  • [1] Olefin-Bond Chemodifferentiation through Cross-Metathesis Reactions: A Stereocontrolled Approach to Functionalized β2,3-Amino Acid Derivatives
    Kardos, Marton
    Kiss, Lorand
    Haukka, Matti
    Fustero, Santos
    Fulop, Ferenc
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (14) : 1894 - 1901
  • [2] Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives
    Kiss, Lorand
    Kardos, Marton
    Vass, Csaba
    Fueloep, Ferenc
    SYNTHESIS-STUTTGART, 2018, 50 (18): : 3571 - 3588
  • [3] Stereocontrolled Synthesis of Difunctionalized Azetidinones and 2,3-Amino Acid Derivatives from Cyclodienes by Ring-Opening and Cross-Metathesis Reactions
    Kardos, MaRton
    Kiss, Lorand
    Fueloep, Ferenc
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (10) : 1155 - 1159
  • [4] Cross-metathesis functionalized exo-olefin derivatives of lactide
    Sinclair, Fern
    Shaver, Michael P.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2018, 56 (07) : 741 - 748
  • [5] Olefin cross-metathesis for the synthesis of heteroaromatic compounds
    Donohoe, Timothy J.
    Bower, John F.
    Chan, Louis K. M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (07) : 1322 - 1328
  • [6] Synthesis of α,β-unsaturated amides by olefin cross-metathesis
    Choi, TL
    Chatterjee, AK
    Grubbs, RH
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (07) : 1277 - 1279
  • [7] Cross-Metathesis Reactions as an Efficient Tool in the Synthesis of Fluorinated Cyclic β-Amino Acids
    Fustero, Santos
    Sanchez-Rosello, Maria
    Luis Acena, Jose
    Fernandez, Begona
    Asensio, Amparo
    Sanz-Cervera, Juan F.
    del Pozo, Carlos
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) : 3414 - 3423
  • [8] Synthesis of chlorophyll a glycoconjugates using olefin cross-metathesis
    Lonin, Ivan S.
    Grin, Mikhail A.
    Lakhina, Anna A.
    Mironov, Andrey F.
    MENDELEEV COMMUNICATIONS, 2012, 22 (03) : 157 - 158
  • [9] Synthesis of vinyl- and allylphosphonates by olefin cross-metathesis
    Chatterjee, AK
    Choi, TL
    Grubbs, RH
    SYNLETT, 2001, : 1034 - 1037
  • [10] Synthesis of vinyl-functionalized thiazoles by cross-metathesis and tandem Stille coupling/cross-metathesis
    Dash, Jyotirmayee
    Arseniyadis, Stellios
    Cossy, Janine
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (1-2) : 152 - 156
12345