Lewis acid mediated diastereoselective intermolecular radical addition/trapping with pyrazolidinone acrylimides

被引:0
|
作者
Ma, Gaoyuan [1 ]
Fujita, Takehiro [2 ]
Sibi, Mukund P. [1 ]
机构
[1] N Dakota State Univ, Dept Chem & Biochem, Fargo, ND 58108 USA
[2] Kyoto Univ, Inst Chem Res, Kyoto 6068501, Japan
关键词
Radical addition/trapping; Pyrazolidinone; Diastereoselectivity; Fluxional chirality; Lewis acid; ALLYLATION REACTIONS; KINETIC RESOLUTION; CHIRAL RELAY; STEREOCHEMISTRY; CYCLIZATION; SELECTIVITY; TEMPLATES;
D O I
10.1016/j.tetlet.2015.02.008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein a new pyrazolidinone chiral auxiliary and its utility in Lewis acid-mediated conjugate addition followed by diastereoselective trapping of the intermediate radical by an allyl group. The allylated products were obtained in good yields (up to 89%) and high diastereoselectivities (up to 94/6). (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3571 / 3574
页数:4
相关论文
共 50 条
  • [31] Intermolecular alkyl radical addition to chiral N-acylhydrazones mediated by manganese carbonyl
    Friestad, GK
    Qin, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) : 9922 - 9923
  • [32] Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts
    Nguyen, John D.
    Tucker, Joseph W.
    Konieczynska, Marlena D.
    Stephenson, Corey R. J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) : 4160 - 4163
  • [33] Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries
    Campari, G
    Fagnoni, M
    Mella, M
    Albini, A
    TETRAHEDRON-ASYMMETRY, 2000, 11 (09) : 1891 - 1906
  • [34] Diastereoselective 1,4-addition of stannyl radical in the presence of Lewis acid: A novel synthetic route to optically active beta-stannyl esters
    Nishida, M
    Nishida, A
    Kawahara, N
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11): : 3574 - 3575
  • [35] Lewis Acid Mediated Addition of Tri-n-Butylstannylmethylisoxazole with Aldehydes
    Yamamoto, M.
    Ohtsuka, K.
    Kishikawa, K.
    Kohmoto, S.
    Synthetic Communications, 26 (11):
  • [36] Radical Conjugate Addition of Acylsilane Enabled by Synergistic Photoredox and Lewis Acid Catalysis
    Guo, Ning
    Luo, Yao
    Feng, Lili
    Liu, Zhili
    Cao, Weidi
    Feng, Xiaoming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (05)
  • [37] Enantioselective radical addition to N-acyl hydrazones mediated by chiral Lewis acids
    Friestad, GK
    Shen, YH
    Ruggles, EL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (41) : 5061 - 5063
  • [38] Arynes as Radical Acceptors: TEMPO-Mediated Cascades Comprising Addition, Cyclization, and Trapping
    Scheruebl, Maximilian
    Daniliuc, Constantin G.
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (02) : 711 - 715
  • [39] Lanthanide Lewis acid-mediated enantioselective conjugate radical additions
    Sibi, MP
    Manyem, S
    ORGANIC LETTERS, 2002, 4 (17) : 2929 - 2932
  • [40] Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines:: a stereoselective approach towards α-amino phosphonates
    Schlemminger, I
    Willecke, A
    Maison, W
    Koch, R
    Lützen, A
    Martens, J
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (21): : 2804 - 2816