Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels-Alder cycloaddition reactions

被引:50
|
作者
Guizzetti, Stefania [1 ]
Benaglia, Maurizio [1 ]
Siegel, Jay S. [2 ]
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
关键词
ORGANIC CATALYSIS; IMIDAZOLIDIN-4-ONE; IMMOBILIZATION; STRATEGIES;
D O I
10.1039/c2cc17919a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Poly(methylhydrosiloxane) (PMHS) supported organic catalysts promoted the Diels-Alder reaction of dienes with alpha,beta-unsaturated aldehydes, also in pure water, in yields and enantiomeric excesses comparable to those observed with the non-supported catalysts (up to 93% ee). Recycling of the catalysts was performed with no loss of enantioselectivity for at least five reaction cycles.
引用
收藏
页码:3188 / 3190
页数:3
相关论文
共 50 条
  • [21] Application of recyclable ionic liquid-supported imidazolidinone catalyst in enantioselective Diels-Alder reactions
    Shen, Zhi-Liang
    Cheong, Hao-Lun
    Lai, Yin-Chang
    Loo, Wan-Yi
    Loh, Teck-Peng
    [J]. GREEN CHEMISTRY, 2012, 14 (09) : 2626 - 2630
  • [22] Air-stable, storable, and highly efficient chiral zirconium catalysts for enantioselective Mannich-type, aza Diels-Alder, aldol, and hetero Diels-Alder reactions
    Kobayashi, S
    Ueno, M
    Saito, S
    Mizuki, Y
    Ishitani, H
    Yamashita, Y
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5476 - 5481
  • [23] Utility of a chiral 1,3-dioxane template in stereoselective intramolecular Diels-Alder reactions
    Evanno, Laurent
    Deville, Alexandre
    Dubost, Lionel
    Chiaroni, Angele
    Bodo, Bernard
    Nay, Bastien
    [J]. TETRAHEDRON LETTERS, 2007, 48 (16) : 2893 - 2896
  • [24] Stereoselective hetero Diels-Alder reactions of chiral tricarbonyl (η6-benzaldehyde)chromium complexes
    Baldoli, C
    Maiorana, S
    Licandro, E
    Zinzalla, G
    Lanfranchi, M
    Tiripicchio, A
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (15) : 2159 - 2167
  • [25] Synthesis of Main-Chain Ionic Polymers of Chiral Imidazolidinone Organocatalysts and Their Application to Asymmetric Diels-Alder Reactions
    Haraguchi, Naoki
    Takenaka, Nagisa
    Najwa, Aisyah
    Takahara, Yuta
    Mun, Mah Kar
    Itsuno, Shinichi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 112 - 123
  • [26] Highly diastereoselective photochemical Diels-Alder reactions: towards the development of a photoactivated chiral auxiliary
    Jones, S
    Atherton, JCC
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (08) : 1117 - 1119
  • [27] A new approach to enantiocontrol and enantioselectivity amplification: Chiral relay in Diels-Alder reactions
    Sibi, MP
    Venkatraman, L
    Liu, M
    Jasperse, CP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) : 8444 - 8445
  • [28] INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLBORANES - A HIGHLY STEREOSELECTIVE 2-STEP DECALIN SYNTHESIS
    SINGLETON, DA
    LEE, YK
    [J]. TETRAHEDRON LETTERS, 1995, 36 (20) : 3473 - 3476
  • [29] IMIDAZOLIDIN-2-ONES AS PRACTICAL, EFFICIENT CHIRAL AUXILIARIES IN DIELS-ALDER REACTIONS
    JENSEN, KN
    ROOS, GHP
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (12) : 1553 - 1554
  • [30] New chiral sultam auxiliaries: preparation and their application in asymmetric Diels-Alder reactions
    Chan, WH
    Lee, AWM
    Jiang, LS
    Mak, TCW
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2501 - 2504