A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions

被引:132
作者
Carswell, Emma L. [1 ]
Snapper, Marc L. [1 ]
Hoveyda, Amir H. [1 ]
机构
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
关键词
asymmetric catalysis; enantioselective synthesis; imines; silver; vinylogous Mannich reactions;
D O I
10.1002/anie.200603496
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS = SiMe3). All that is needed is commercially available AgOAc, a readily available amino acid derived phosphine, and a commercially available or easily prepared (one step) siloxyfuran. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7230 / 7233
页数:4
相关论文
共 28 条
  • [21] Direct catalytic asymmetric Mannich-type reaction of hydroxyketone using a Et2Zn/Linked-BINOL complex:: Synthesis of either anti- or syn-β-amino alcohols
    Matsunaga, S
    Yoshida, T
    Morimoto, H
    Kumagai, N
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) : 8777 - 8785
  • [22] π-nucleophilicity in carbon-carbon bond-forming reactions
    Mayr, H
    Kempf, B
    Ofial, AR
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (01) : 66 - 77
  • [23] Highly enantioselective Cr(salen)-catalyzed reaction of 2-(trimethylsilyloxy)furan and aldehydes. Effect of alcohol on enantioselectivity
    Onitsuka, S
    Matsuoka, Y
    Irie, R
    Katsuki, T
    [J]. CHEMISTRY LETTERS, 2003, 32 (10) : 974 - 975
  • [24] Three-component catalytic asymmetric synthesis of aliphatic amines
    Porter, JR
    Traverse, JF
    Hoveyda, AH
    Snapper, ML
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) : 10409 - 10410
  • [25] The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids:: Enantioselective synthesis of β-amino acids
    Song, Jun
    Wang, Yi
    Deng, Li
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) : 6048 - 6049
  • [26] Vinylogous Mannich reactions.: Additions of trimethylsilyloxyfuran to fluorinated aldimines
    Spanedda, MV
    Ourévitch, M
    Crousse, B
    Bégué, JP
    Bonnet-Delpon, D
    [J]. TETRAHEDRON LETTERS, 2004, 45 (26) : 5023 - 5025
  • [27] Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan
    Uraguchi, D
    Sorimachi, K
    Terada, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) : 11804 - 11805
  • [28] Enantioselective silyl protection of alcohols catalysed by an amino-acid-based small molecule
    Zhao, Yu
    Rodrigo, Jason
    Hoveyda, Amir H.
    Snapper, Marc L.
    [J]. NATURE, 2006, 443 (7107) : 67 - 70