Catalytic enantioselective addition of nitro compounds to imines -: A simple approach for the synthesis of optically active β-nitro-α-amino esters

被引:2
|
作者
Nishiwaki, N [1 ]
Knudsen, KR [1 ]
Gothelf, KV [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Met Catalyzed React, DK-8000 Aarhus C, Denmark
关键词
amino acids; asymmetric catalysis; imines; Lewis acids; nitro compounds;
D O I
10.1002/1521-3773(20010817)40:16<2992::AID-ANIE2992>3.0.CO;2-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic and asymmetric nitro-Mannich reaction of nitro compounds to α-imino esters catalyzed by chiral bisoxazoline-copper complexes [Eq. (1); Pg = protecting group] gave β-nitro-α-amino esters with excellent diastereo- and enantioselectivities. The reactions can be performed under ambient conditions.
引用
收藏
页码:2992 / 2995
页数:4
相关论文
共 50 条
  • [1] Catalytic enantioselective addition of nitro compounds to imines - A simple approach for the synthesis of optically active β-nitro-α-amino esters
    Nishiwaki, Nagatoshi
    Knudsen, Kristian Rahbek
    Gothelf, Kurt V.
    Jrgensen, Karl Anker
    2001, Wiley-VCH Verlag (40)
  • [2] Catalytic asymmetric Henry reactions -: a simple approach to optically active β-nitro α-hydroxy esters
    Christensen, C
    Juhl, K
    Jorgensen, KA
    CHEMICAL COMMUNICATIONS, 2001, (21) : 2222 - 2223
  • [3] Organocatalytic conjugate addition of α-nitroacetates to β,γ-unsaturated α-keto esters and subsequent decarboxylation: synthesis of optically active δ-nitro-α-keto esters
    Lu, Rui-jiong
    Wei, Wen-tao
    Wang, Jin-jia
    Nie, Shao-zhen
    Zhang, Xue-jing
    Yan, Ming
    TETRAHEDRON, 2012, 68 (46) : 9397 - 9404
  • [4] Formation of optically active aromatic α-amino acids by catalytic enantioselective addition of imines to aromatic compounds
    Saaby, S
    Fang, XM
    Gathergood, N
    Jorgensen, KA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (22) : 4114 - 4116
  • [5] Formation of optically active aromatic α-amino acids by catalytic enantioselective addition of imines to aromatic compounds
    Saaby, Steen
    Fang, Xiangming
    Gathergood, Nicholas
    Jorgensen, Karl Anker
    Angewandte Chemie (International Edition in English), 2000, 39 (22): : 4114 - 4116
  • [6] Catalytic enantioselective ene reactions of imines:: a simple approach for the formation of optically active α-amino acids
    Yao, SL
    Fang, XM
    Jorgensen, KA
    CHEMICAL COMMUNICATIONS, 1998, (22) : 2547 - 2548
  • [7] Copper-catalyzed enantioselective Henry reactions of α-keto esters:: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters
    Christensen, C
    Juhl, K
    Hazell, RG
    Jorgensen, KA
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4875 - 4881
  • [8] The first catalytic asymmetric aza-Henry reaction of nitronates with imines:: A novel approach to optically active β-nitro-α-amino acid- and α,β-diamino acid derivatives
    Knudsen, KR
    Risgaard, T
    Nishiwaki, N
    Gothelf, KV
    Jorgensen, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) : 5843 - 5844
  • [9] Catalytic approach for the formation of optically active allyl α-amino acids by addition of allylic metal compounds to α-imino esters
    Fang, XM
    Johannsen, M
    Yao, SL
    Gathergood, N
    Hazell, RG
    Jorgensen, KA
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13): : 4844 - 4849
  • [10] A new catalytic enantioselective approach to optically active lactones by addition reactions to α-dicarbonyl compounds
    Audrain, H
    Jorgensen, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11543 - 11544