Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters

被引:39
作者
Vecchione, Matthew K. [1 ]
Li, Le [1 ]
Seidel, Daniel [1 ]
机构
[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
关键词
AMINO ACID-DERIVATIVES; QUATERNARY AMMONIUM-SALTS; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; NONADJACENT STEREOCENTERS; CONJUGATE ADDITION; EFFICIENT APPROACH; CYCLIC-PEPTIDES; BOND DONORS; SCHIFF-BASE;
D O I
10.1039/c0cc00556h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A readily available bifunctional thiourea catalyst promotes aldol additions of alpha-isothiocyanato imides to alpha-ketoesters under mild reaction conditions to form beta-hydroxy-alpha-amino acid derivatives with high levels of enantioselectivity.
引用
收藏
页码:4604 / 4606
页数:3
相关论文
共 72 条
  • [41] The advent and development of organocatalysis
    MacMillan, David W. C.
    [J]. NATURE, 2008, 455 (7211) : 304 - 308
  • [42] Lobocyclamide B from Lyngbya confervoides.: Configuration and asymmetric synthesis of β-hydroxy-α-amino acids by (-)-sparteine-mediated aldol addition
    MacMillan, JB
    Molinski, TF
    [J]. ORGANIC LETTERS, 2002, 4 (11) : 1883 - 1886
  • [43] Stereoselective synthesis of anti-β-hydroxy-α-amino acids through dynamic kinetic resolution
    Makino, K
    Goto, T
    Hiroki, Y
    Hamada, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) : 882 - 884
  • [44] Cupreines and cupreidines: An emerging class of bifunctional cinchona organocatalysts
    Marcelli, Tommaso
    van Maarseveen, Jan H.
    Hiemstra, Henk
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) : 7496 - 7504
  • [45] Catalytic asymmetric synthesis of α-amino acids
    Najera, Carmen
    Sansano, Jose M.
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4584 - 4671
  • [46] Nicolaou KC, 1999, ANGEW CHEM INT EDIT, V38, P2096, DOI 10.1002/(SICI)1521-3773(19990802)38:15<2096::AID-ANIE2096>3.0.CO
  • [47] 2-F
  • [48] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts
    Okino, T
    Hoashi, Y
    Takemoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) : 12672 - 12673
  • [49] Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts
    Ooi, T
    Kameda, M
    Taniguchi, M
    Maruoka, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9685 - 9694
  • [50] Ooi T, 2002, ANGEW CHEM INT EDIT, V41, P4542, DOI 10.1002/1521-3773(20021202)41:23<4542::AID-ANIE4542>3.0.CO