Asymmetric counteranion-directed catalysis for the epoxidation of enals

被引：181
作者：
Wang, Xingwang [1 ]
List, Benjamin [1 ]
机构：
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 06期
关键词：
aldehydes; asymmetric epoxidation; chiral phosphates; enals; organocatalysis;
D O I：
10.1002/anie.200704185
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) A new mode of chiral anion catalysis: A powerful chiral-counteranion strategy for catalytic asymmetric epoxidations using the newly discovered catalyst 1 has been applied to the epoxidation of α,β-unsaturated aldehydes together with tert-butyl hydroperoxide as the oxidant (see scheme). Remarkably, this system provides the corresponding epoxides in high diastereo- and enantioselectivity for both di- and trisubstituted enals. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：1119 / 1122
页数：4
相关论文
共 97 条
  • [1] Synthetic applications of nonmetal catalysts for homogeneous oxidations
    Adam, W
    Saha-Möller, CR
    Ganeshpure, PA
    [J]. CHEMICAL REVIEWS, 2001, 101 (11) : 3499 - 3548
  • [2] Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates
    Adamo, MFA
    Aggarwal, VK
    Sage, MA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8317 - 8318
  • [3] Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain
    Adger, BM
    Barkley, JV
    Bergeron, S
    Cappi, MW
    Flowerdew, BE
    Jackson, MP
    McCague, R
    Nugent, TC
    Roberts, SM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23): : 3501 - 3507
  • [4] New insights in the mechanism of amine catalyzed epoxidation: Dual role of protonated ammonium salts as both phase transfer catalysts and activators of Oxone
    Aggarwal, VK
    Lopin, C
    Sandrinelli, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) : 7596 - 7601
  • [5] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity
    Akiyama, T
    Tamura, Y
    Itoh, J
    Morita, H
    Fuchibe, K
    [J]. SYNLETT, 2006, (01) : 141 - 143
  • [6] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL
    Akiyama, T
    Saitoh, Y
    Morita, H
    Fuchibe, K
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1523 - 1526
  • [7] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
    Akiyama, T
    Morita, H
    Itoh, J
    Fuchibe, K
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
  • [8] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [9] Akiyama T., 2006, Patent, Patent No. [EP1623971A1, 1623971]
  • [10] Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240
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