C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions

被引:78
作者
Bolm, C [1 ]
Martin, M [1 ]
Simic, O [1 ]
Verrucci, M [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
D O I
10.1021/ol027273e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Bissulfoximines have been used as chiral ligands in copper-catalyzed enantioselective Diels-Alder reactions between acryloyl-2-oxazolidinones and cyclopentadiene. After optimizing the ligand structure, the metal source, the counterions, and the solvent, products with up to 93% ee have been obtained.
引用
收藏
页码:427 / 429
页数:3
相关论文
共 34 条
  • [1] [Anonymous], 1998, TRANSITION METALS OR
  • [2] [Anonymous], ANGEW CHEM
  • [3] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF ALDEHYDES
    BOLM, C
    MULLER, P
    [J]. TETRAHEDRON LETTERS, 1995, 36 (10) : 1625 - 1628
  • [4] Bolm C, 2002, SYNTHESIS-STUTTGART, P879
  • [5] Bolm C, 2001, SYNLETT, P1878
  • [6] Highly enantioselective hetero-Diels-Alder reactions catalyzed by a C2-symmetric bis(sulfoximine) Copper(II) complex
    Bolm, C
    Simic, O
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) : 3830 - 3831
  • [7] BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS
    BOLM, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05): : 542 - 543
  • [8] Bolm C, 1996, SYNLETT, P775
  • [9] Sulfoximine-titanium reagents in enantioselective trimethylsilylcyanations of aldehydes
    Bolm, C
    Muller, P
    Harms, K
    [J]. ACTA CHEMICA SCANDINAVICA, 1996, 50 (04): : 305 - 315
  • [10] Optically active sulfoximines in enantioselective palladium catalysis
    Bolm, C
    Kaufmann, D
    Zehnder, M
    Neuburger, M
    [J]. TETRAHEDRON LETTERS, 1996, 37 (23) : 3985 - 3988