A highly enantioselective asymmetric Darzens reaction catalysed by proline based efficient organocatalysts for the synthesis of di- and tri-substituted epoxides

被引：12
作者：
Ashokkumar, Veeramanoharan [1 ]
Siva, Ayyanar [1 ]
Chidambaram, R. Ramaswamy [1 ]
机构：
[1] Madurai Kamaraj Univ, Sch Chem, Dept Inorgan Chem, Supramol & Organometall Chem Lab, Madurai 625021, Tamil Nadu, India
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 79期
关键词：
PHASE-TRANSFER CATALYSIS; GLYCIDIC AMIDES; ALPHA; BETA-UNSATURATED KETONES; DIASTEREOSELECTIVE SYNTHESIS; AROMATIC-ALDEHYDES; CARBONYL-COMPOUNDS; BETA-EPOXY KETONES; EPOXIDATION REACTIONS; HYDROGEN-PEROXIDE; AMMONIUM YLIDES;
D O I：
10.1039/c7cc06194c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new class of easily available and readily tunable proline based chiral organocatalysts was found to efficiently catalyse an unprecedented highly enantioselective asymmetric Darzens reaction of alpha-chloroketones and substituted alpha-chloroketones with various aldehydes, which directly produces optically active di- and tri- substituted chiral epoxides with higher product yields (up to 97%) and excellent ee's (up to 99%) under mild reaction conditions.
引用
收藏
页码：10926 / 10929
页数：4
相关论文
共 81 条
  • [1] Enantio- and diastereoselective Darzens condensations
    Achard, Thierry J. R.
    Belokon', Yuri N.
    Ilyin, Michael
    Moskalenko, Margarita
    North, Michael
    Pizzato, Francesca
    [J]. TETRAHEDRON LETTERS, 2007, 48 (17) : 2965 - 2969
  • [2] Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis
    Aggarwal, VK
    Charmant, JPH
    Fuentes, D
    Harvey, JN
    Hynd, G
    Ohara, D
    Picoul, W
    Robiette, R
    Vasse, JL
    Winn, CL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) : 2105 - 2114
  • [3] Highly enantioselective Darzens reaction of a camphor-derived sulfonium amide to give glycidic amides and their applications in synthesis
    Aggarwal, VK
    Hynd, G
    Picoul, W
    Vasse, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) : 9964 - 9965
  • [4] Enantioselective Aza-Darzens Reaction Catalyzed by A Chiral Phosphoric Acid
    Akiyama, Takahiko
    Suzuki, Tohru
    Mori, Keiji
    [J]. ORGANIC LETTERS, 2009, 11 (11) : 2445 - 2447
  • [5] Strained azetidinium ylides: new reagents for epoxidation
    Alex, Audrey
    Larmanjat, Benedicte
    Marrot, Jerome
    Couty, Francois
    David, Olivier
    [J]. CHEMICAL COMMUNICATIONS, 2007, (24) : 2500 - 2502
  • [6] Phase-transfer-catalyzed asymmetric Darzens reaction using a new chiral ammonium salt
    Arai, S
    Tokumaru, K
    Aoyama, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (09) : 1845 - 1848
  • [7] Asymmetric Darzens reaction utilizing chloromethyl phenyl sulfone under phase-transfer catalyzed conditions
    Arai, S
    Shioiri, T
    [J]. TETRAHEDRON, 2002, 58 (07) : 1407 - 1413
  • [8] Diastereoselective Darzens reactions of α-chloroesters, amides and nitriles with aromatic aldehydes under phase-transfer catalyzed conditions
    Arai, S
    Suzuki, Y
    Tokumaru, K
    Shioiri, T
    [J]. TETRAHEDRON LETTERS, 2002, 43 (05) : 833 - 836
  • [9] Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions
    Arai, S
    Shioiri, T
    [J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2145 - 2148
  • [10] Phase-transfer-catalyzed asymmetric Darzens reaction
    Arai, S
    Shirai, Y
    Ishida, T
    Shioiri, T
    [J]. TETRAHEDRON, 1999, 55 (20) : 6375 - 6386
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