Vanadium-catalyzed asymmetric epoxidation: Proline-derived hydroxamic acids revisited

被引:9
|
作者
Bourhani, Zainaba [1 ]
Malkov, Andrei V. [1 ]
机构
[1] Univ Glasgow, Dept Chem, WestChem, Glasgow G12 8QQ, Lanark, Scotland
关键词
asymmetric catalysis; epoxidations; homogeneous catalysis; ligands; vanadium;
D O I
10.1055/s-2006-956494
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Structural features of ligands and substrates affecting enantioselectivity in vanadium (V)-catalyzed epoxidation of allylic alcohols were investigated. For the hydroxamic acid ligands derived from arylhydroxylamines, 2-aryl-substituted allylic alcohols emerged as the best substrates furnishing good level of enantioselectivity.
引用
收藏
页码:3525 / 3528
页数:4
相关论文
共 50 条
  • [41] Probing the "additive effect" in the proline and proline hydroxamic acid catalyzed asymmetric addition of nitroalkanes to cyclic enones
    Hanessian, S
    Govindan, S
    Warrier, JS
    CHIRALITY, 2005, 17 (09) : 540 - 543
  • [42] Heterogeneous vanadium-catalyzed oxidative cleavage of olefins for sustainable synthesis of carboxylic acids
    Upadhyay, Rahul
    Rana, Rohit
    Sood, Aakriti
    Singh, Vikash
    Kumar, Rahul
    Srivastava, Vimal Chandra
    Maurya, Sushil K.
    CHEMICAL COMMUNICATIONS, 2021, 57 (44) : 5430 - 5433
  • [43] Studies on the Vanadium-Catalyzed Nonoxidative Depolymerization of Miscanthus giganteus-Derived Lignin
    Chan, Julian M. W.
    Bauer, Stefan
    Sorek, Hagit
    Sreekumar, Sanil
    Wang, Kun
    Toste, F. Dean
    ACS CATALYSIS, 2013, 3 (06): : 1369 - 1377
  • [44] Vanadium-catalyzed asymmetric oxidation of α-hydroxy esters using molecular oxygen as stoichlometric oxidant
    Radosevich, AT
    Musich, C
    Toste, FD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1090 - 1091
  • [45] STEREOSELECTIVE VANADIUM-CATALYZED EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES POSSESSING A NEIGHBORING HYDROXY GROUP
    GLOTTER, E
    ZVIELY, M
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (02): : 327 - 331
  • [46] (S)-proline-derived chiral ligands bearing organosulfur or -selenenyl groups as coordinating elements in palladium-catalyzed asymmetric allylic alkylations
    Suzuki, Y
    Abe, I
    Hiroi, K
    HETEROCYCLES, 1999, 50 (01) : 89 - 94
  • [47] REARRANGEMENT OF A HINDERED ALLYLIC ALCOHOL DURING VANADIUM-CATALYZED EPOXIDATION - A SHORT SYNTHESIS OF UVIDIN-C
    ZIEGLER, FE
    JAYNES, BH
    TETRAHEDRON LETTERS, 1985, 26 (48) : 5875 - 5878
  • [48] Vanadium-Catalyzed Asymmetric Oxidation of Sulfides Using Schiff Base Ligands Derived from β-Amino Alcohols with Two Stereogenic Centers
    Wu, Yinuo
    Liu, Juntao
    Li, Xingshu
    Chan, Albert S. C.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (16) : 2607 - 2610
  • [49] Dipeptidic Proline-Derived Thiourea Organocatalysts for Asymmetric Michael addition Reactions between Aldehydes and Nitroolefins
    Yeo, Hyoung Min
    Kim, Taek Hyeon
    CHEMISTRYSELECT, 2024, 9 (32):
  • [50] Asymmetric Lewis Acid Mediated [1,2]-Rearrangement of Proline-Derived Ammonium Ylides
    Tuzina, Pavel
    Somfai, Peter
    ORGANIC LETTERS, 2009, 11 (04) : 919 - 921