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
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 04期
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 50 条
  • [1] Ethylene-bridged bissulfoximines in copper-catalyzed enantioselective hetero-Diels-Alder reactions
    Bolm, C
    Verrucci, M
    Simic, O
    Hackenberger, CPR
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1696 - 1700
  • [2] Copper-Catalyzed Diels-Alder Reactions
    Reymond, Sebastien
    Cossy, Janine
    CHEMICAL REVIEWS, 2008, 108 (12) : 5359 - 5406
  • [3] Pseudo-C3-symmetric trisoxazolines as ligands in copper catalyzed enantioselective Diels-Alder reaction
    Zhou, J
    Tang, Y
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (03) : 429 - 433
  • [4] C2-Symmetric bipyrrolidines as organocatalysts for asymmetric Diels-Alder reactions
    Ma, Yuanhui
    Zhang, Yong Jian
    Jin, Shangbin
    Li, Qiqi
    Li, Chenguang
    Lee, Junseong
    Zhang, Wanbin
    TETRAHEDRON LETTERS, 2009, 50 (52) : 7388 - 7391
  • [5] Highly enantioselective hetero-Diels-Alder reactions catalyzed by a C2-symmetric bis(sulfoximine) Copper(II) complex
    Bolm, C
    Simic, O
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (16) : 3830 - 3831
  • [6] Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
    Jiang, Bing
    Liang, Qiu-Ju
    Han, Yu
    Zhao, Meng
    Xu, Yun-He
    Loh, Teck-Peng
    ORGANIC LETTERS, 2018, 20 (11) : 3215 - 3219
  • [7] A new class of C1-symmetric monosulfoximine ligands for enantioselective hetero Diels-Alder reactions
    Bolm, C
    Verrucci, M
    Simic, O
    Cozzi, PG
    Raabe, G
    Okamura, H
    CHEMICAL COMMUNICATIONS, 2003, (22) : 2826 - 2827
  • [8] Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding
    Thadani, AN
    Stankovic, AR
    Rawal, VH
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5846 - 5850
  • [9] Chiral C2-symmetric CuII complexes as catalysts for enantioselective hetero-Diels-Alder reactions
    Evans, DA
    Olhava, EJ
    Johnson, JS
    Janey, JM
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (24) : 3372 - 3375
  • [10] C1-symmetric versus C2-symmetric ligands in enantioselective copper-bis(oxazoline)-catalyzed cyclopropanation reactions
    Fraile, Jose M.
    Garcia, Jose I.
    Gissibl, Anja
    Mayoral, Jose A.
    Pires, Elisabet
    Reiser, Oliver
    Roldan, Marta
    Villalba, Isabel
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (31) : 8830 - 8839
12345