Non-C2-symmetric, chirally economical, and readily tunable linked-binols:: Design and application in a direct catalytic asymmetric Mannich-type reaction

被引：68
作者：
Yoshida, T [1 ]
Morimoto, H [1 ]
Kumagai, N [1 ]
Matsunaga, S [1 ]
Shibasaki, M [1 ]
机构：
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 22期
关键词：
amino alcohols; asymmetric catalysis; chiral ligands; Mannich reaction; zinc;
D O I：
10.1002/anie.200500425
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) An achiral unit is shown to be better than a chiral unit in promoting an asymmetric reaction. Non-C2-symmetric linked-binols 1 with one chiral 1,1′-bi-2-naphthol unit and one flexible achiral unit are employed as ligands in direct catalytic asymmetric Mannich-type reactions (see scheme; TON = turnover number). With as little as 0.01 mol% of ligand 1 a and 0.04 mol% of Et2Zn, the reaction proceeded smoothly to give the product in 98% ee. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：3470 / 3474
页数：5
相关论文
共 55 条
  • [1] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
  • [2] [Anonymous], 2003, COMPREHENSIVE ASYMME
  • [3] The use of achiral ligands to convey asymmetry: Chiral environment amplification
    Balsells, J
    Walsh, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1802 - 1803
  • [4] Kinetic aspects of nonlinear effects in asymmetric catalysis
    Blackmond, DG
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 402 - 411
  • [5] Modified BINOL ligands in asymmetric catalysis
    Chen, Y
    Yekta, S
    Yudin, AK
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3155 - 3211
  • [6] The direct catalytic asymmetric Mannich reaction
    Córdova, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (02) : 102 - 112
  • [7] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives
    Córdova, A
    Watanabe, S
    Tanaka, F
    Notz, W
    Barbas, CF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1866 - 1867
  • [8] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids
    Córdova, A
    Notz, W
    Zhong, GF
    Betancort, JM
    Barbas, CF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1842 - 1843
  • [9] Chiral poisoning and asymmetric activation
    Faller, JW
    Lavoie, AR
    Parr, J
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3345 - 3367
  • [10] FISCHLI A, 1976, CHIMIA, V30, P4
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