Synthesis and applications of chiral bis-THF in asymmetric synthesis

被引:18
作者
Alexakis, A [1 ]
Tomassini, A [1 ]
Leconte, S [1 ]
机构
[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland
关键词
asymmetric synthesis; chirality; diether; organolithium reagents; coordination;
D O I
10.1016/j.tet.2004.07.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of enantiopure bis-THF is described, starting from D-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9479 / 9484
页数:6
相关论文
共 55 条
  • [1] Alexakis A, 1998, SYNLETT, P1165
  • [2] Chiral aminals: Powerful auxiliaries in asymmetric synthesis
    Alexakis, A
    Mangeney, P
    Lensen, N
    Tranchier, JP
    Gosmini, R
    Raussou, S
    [J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (03) : 531 - 534
  • [3] Alexakis A, 2000, ANGEW CHEM INT EDIT, V39, P4093, DOI 10.1002/1521-3773(20001117)39:22<4093::AID-ANIE4093>3.0.CO
  • [4] 2-R
  • [5] Alexakis A., 1996, ADV ASYMMETRIC SYNTH, P93
  • [6] ALEXAKIS A, 1998, ORG SYNTH, V76, P23
  • [7] Asymmetric addition of organolithium reagents to prochiral arene tricarbonylchromium complexes
    Amurrio, D
    Khan, K
    Kundig, EP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2258 - 2259
  • [8] Enantioselective addition of organolithium reagents to imines mediated by C2-symmetric bis(aziridine) ligands
    Andersson, PG
    Johansson, F
    Tanner, D
    [J]. TETRAHEDRON, 1998, 54 (38) : 11549 - 11566
  • [9] Synthesis of enantiomerically enriched amines by chiral ligand mediated addition of organolithium reagents to imines
    Arrasate, S
    Lete, E
    Sotomayor, N
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (14) : 2077 - 2082
  • [10] ASYMMETRIC ADDITION TO CHIRAL NAPHTHYLOXAZOLINES - A FACILE ROUTE TO 1,1,2-TRISUBSTITUTED-1,2-DIHYDRONAPHTHALENES IN HIGH ENANTIOMERIC EXCESS
    BARNER, BA
    MEYERS, AI
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) : 1865 - 1866