Recent developments in asymmetric catalytic addition to C=N bonds

被引:418
作者
Friestad, Gregory K. [1 ]
Mathies, Alex K. [1 ]
机构
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
基金
日本学术振兴会;
关键词
MANNICH-TYPE REACTIONS; ENANTIOSELECTIVE DIETHYLZINC ADDITION; ALPHA-AMINO-ACIDS; HIGHLY STEREOSELECTIVE-SYNTHESIS; AZA-DARZENS REACTION; CHIRAL N-ACYLHYDRAZONES; REISSERT-TYPE REACTION; C-H BONDS; NEUTRAL COORDINATE-ORGANOCATALYSTS; OPTICALLY-ACTIVE HOMOALLYLAMINES;
D O I
10.1016/j.tet.2006.11.076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methods for enantioselective C-C bond constructions via additions to imines and related compounds are reviewed, with an emphasis on the most recent efforts involving asymmetric catalysis. Selected seminal examples are provided in order to place the recent developments in context. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2541 / 2569
页数:29
相关论文
共 317 条
  • [31] Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand
    Boezio, AA
    Pytkowicz, J
    Côté, A
    Charette, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) : 14260 - 14261
  • [32] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines
    Boezio, AA
    Charette, AB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) : 1692 - 1693
  • [33] Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives
    Burger, Erin C.
    Tunge, Jon A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) : 10002 - 10003
  • [34] Simple 1,2-diamine ligands for asymmetric addition of aryllithium reagents to imines
    Cabello, N
    Kizirian, JC
    Gille, S
    Alexakis, A
    Bernardinelli, G
    Pinchard, L
    Caille, JC
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) : 4835 - 4842
  • [35] Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam
    Cantrill, AA
    Hall, LD
    Jarvis, AN
    Osborn, HMI
    Raphy, J
    Sweeney, JB
    [J]. CHEMICAL COMMUNICATIONS, 1996, (23) : 2631 - 2632
  • [36] Chen GM, 1999, ANGEW CHEM INT EDIT, V38, P825, DOI 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO
  • [37] 2-V
  • [38] Expedient synthesis of chiral 1,2- and 1,4-diamines: Protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions
    Chowdari, Naidu S.
    Ahmad, Moballigh
    Albertshofer, Klaus
    Tanaka, Fujie
    Barbas, Carlos F., III
    [J]. ORGANIC LETTERS, 2006, 8 (13) : 2839 - 2842
  • [39] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
    Cobb, AJA
    Shaw, DM
    Longbottom, DA
    Gold, JB
    Ley, SV
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96
  • [40] Very mild, enantioselective synthesis of propargylamines catalyzed by copper(I)-bisimine complexes
    Colombo, F
    Benaglia, M
    Orlandi, S
    Usuelli, F
    Celentano, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) : 2064 - 2070