Bi(OTf)3-Catalyzed Diastereoselective One-Pot Synthesis of 1,3-Diamines with Three Continuous Stereogenic Centers

被引:14
作者
Halli, Juliette [1 ]
Kramer, Philipp [3 ]
Grimmer, Jennifer [3 ]
Bolte, Michael [2 ]
Manolikakes, Georg [3 ]
机构
[1] Goethe Univ Frankfurt Main, Inst Organ Chem & Chem Biol, Max von Laue Str 7, D-60438 Frankfurt, Germany
[2] Goethe Univ Frankfurt Main, Inst Inorgan & Analyt Chem, Max von Laue Str 7, D-60438 Frankfurt, Germany
[3] Tech Univ Kaiserslautern, Inst Organ Chem, Erwin Schrodinger Str Geb 54, D-67663 Kaiserslautern, Germany
关键词
AMINO-ACID DERIVATIVES; STEREODIVERGENT SYNTHESIS; 3-COMPONENT SYNTHESIS; BRONSTED ACID; TRIFLIC ACID; CATALYSIS; ENAMIDES; IMINES; ORGANOCATALYSIS; NUCLEOPHILES;
D O I
10.1021/acs.joc.8b01925
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly modular, diastereoselective one-pot-synthesis of 1,3-diamines with three contiguous stereogenic centers is reported. Our method provides a fast and efficient access to 1,2-anti-2,3-anti-1,3-diamines from three readily available building blocks. This Bi(OTf)(3)-catalyzed reaction is insensitive to air and moisture and can be performed on a multigram scale.
引用
收藏
页码:12007 / 12022
页数:16
相关论文
共 51 条
  • [1] [Anonymous], 2002, X AREA DIFFRACTOMETE
  • [2] Enamide Derivatives: Versatile Building Blocks for Highly Functionalized α,β-Substituted Amines
    Bernadat, Guillaume
    Masson, Geraldine
    [J]. SYNLETT, 2014, 25 (20) : 2842 - 2867
  • [3] Applications of bismuth(III) compounds in organic synthesis
    Bothwell, Jason M.
    Krabbe, Scott W.
    Mohan, Ram S.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (09) : 4649 - 4707
  • [4] Enamides: valuable organic substrates
    Carbery, David R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) : 3455 - 3460
  • [5] Christmann M., 2007, ASYMMETRIC SYNTHESIS
  • [6] Chiral Bronsted Acid-Catalyzed Enantioselective Multicomponent Mannich Reaction: Synthesis of anti-1,3-Diamines Using Enecarbamates as Nucleophiles
    Dagousset, Guillaume
    Drouet, Fleur
    Masson, Geraldine
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2009, 11 (23) : 5546 - 5549
  • [7] Antivirals: Past, present and future
    De Clercq, Erik
    [J]. BIOCHEMICAL PHARMACOLOGY, 2013, 85 (06) : 727 - 744
  • [8] DUKE SO, 2011, BIOCH PHYSL, V100, P41, DOI DOI 10.1016/J.PESTBP.2011.02.002
  • [9] Diastereo- and enantioselective synthesis of C-2-symmetric, protected 1,n-diamines from dialdehydes
    Enders, D
    Meiers, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (19): : 2261 - 2263
  • [10] Ascaulitoxin, a phytotoxic bis-amino acid N-glucoside from Ascochyta caulina
    Evidente, A
    Capasso, R
    Cutignano, A
    Taglialatela-Scafati, O
    Vurro, M
    Zonno, MC
    Motta, A
    [J]. PHYTOCHEMISTRY, 1998, 48 (07) : 1131 - 1137