Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

被引:7
作者
Bautista-Hernandez, Claudia I. [1 ]
Cordero-Rivera, Reyna E. [1 ]
Zuniga-Estrada, Erick A. [1 ]
Trejo-Carbajal, Nayely [1 ]
Melendez-Rodriguez, Myriam [1 ]
Suarez-Castillo, Oscar R. [1 ]
Sanchez-Zavala, Maricruz [1 ]
Morales-Rios, Martha S. [2 ]
Joseph-Nathan, Pedro [2 ]
机构
[1] Univ Autonoma Estado Hidalgo, Area Acad Quim, Hidalgo 42184, Mexico
[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Apartado 14-740, Mexico City 07000, DF, Mexico
关键词
CHIRALITY METHOD; RICE BRAN; ACID; NMR;
D O I
10.1016/j.tetasy.2016.06.004
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A convenient and reliable approach for the absolute configuration assignment of oxindole derivatives 2a-m by vibrational circular dichroism (VCD) measurements and evaluation of the VCD bisignated couplet resulting from the interaction of the C2 and C9 carbonyl groups is presented. The absolute configuration assignments were further tested by H-1 NMR measurements and by X-ray diffraction analysis. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:623 / 638
页数:16
相关论文
共 36 条
  • [1] Bicamphor: A Prototypic Molecular System to Investigate Vibrational Excitons
    Abbate, Sergio
    Mazzeo, Giuseppe
    Meneghini, Silvia
    Longhi, Giovanna
    Boiadjiev, Stefan E.
    Lightner, David A.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (18) : 4261 - 4267
  • [2] Enantiodivergent preparation of optically active oxindoles having a stereogenic quaternary carbon center at the C3 position via the lipase-catalyzed desymmetrization protocol: Effective use of 2-furoates for either enzymatic esterification or hydrolysis
    Akai, S
    Tsujino, T
    Akiyama, E
    Tanimoto, K
    Naka, T
    Kita, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2478 - 2486
  • [3] Structures of Spiroindicumides A and B, Unprecedented Carbon Skeletal Spirolactones, and Determination of the Absolute Configuration by Vibrational Circular Dichroism Exciton Approach
    Asai, Teigo
    Taniguchi, Tohru
    Yamamoto, Takashi
    Monde, Kenji
    Oshima, Yoshiteru
    [J]. ORGANIC LETTERS, 2013, 15 (17) : 4320 - 4323
  • [4] Structure Elucidation and Absolute Stereochemistry of Isomeric Monoterpene Chromane Esters
    Batista, Joao M., Jr.
    Batista, Andrea N. L.
    Mota, Jonas S.
    Cass, Quezia B.
    Kato, Massuo J.
    Bolzani, Vanderlan S.
    Freedman, Teresa B.
    Lopez, Silvia N.
    Furlan, Maysa
    Nafie, Laurence A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) : 2603 - 2612
  • [5] The absolute configuration of angular 3′-acyloxypyranocoumarins by vibrational circular dichroism exciton chirality
    Buendia-Trujillo, Abigail I.
    Martin Torrres-Valencia, J.
    Joseph-Nathan, Pedro
    Burgueno-Tapia, Eleuterio
    [J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (20-21) : 1418 - 1423
  • [6] Formal synthesis of (-)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality
    Cordero-Rivera, Reyna E.
    Melendez-Rodriguez, Myriam
    Suarez-Castillo, Oscar R.
    Bautista-Hernandez, Claudia I.
    Trejo-Carbajal, Nayely
    Cruz-Borbolla, Julian
    Castelan-Duarte, Luis E.
    Morales-Rios, Martha S.
    Joseph-Nathan, Pedro
    [J]. TETRAHEDRON-ASYMMETRY, 2015, 26 (14) : 710 - 720
  • [7] Determination of the Absolute Configurations Using Exciton Chirality Method for Vibrational Circular Dichroism: Right Answers for the Wrong Reasons?
    Covington, Cody L.
    Nicu, Valentin P.
    Polayarapu, Prasad L.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (42) : 10589 - 10601
  • [8] Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis
    Cravotto, Giancarlo
    Giovenzana, Giovanni B.
    Palmisano, Giovanni
    Penoni, Andrea
    Pilati, Tullio
    Sisti, Massimo
    Stazi, Federica
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (22) : 3070 - 3074
  • [9] STUDIES OF SOUTH-AFRICAN MEDICINAL-PLANTS .5. AN OXINDOLE FROM THE ROOTS OF CAPPARIS-TOMENTOSA
    DEKKER, TG
    FOURIE, TG
    MATTHEE, E
    SNYCKERS, FO
    [J]. PHYTOCHEMISTRY, 1987, 26 (06) : 1845 - 1846
  • [10] Efficient asymmetric synthesis of novel gastrin receptor antagonist AG-041R via highly stereoselective alkylation of oxindole enolates
    Emura, Takashi
    Esaki, Toru
    Tachibana, Kazutaka
    Shimizu, Makoto
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) : 8559 - 8564