Dibutyltin dimethoxide and BINAP•silver(I) complex-catalyzed asymmetric aldol reaction of alkenyl trichloro acetates with aldehydes

被引:10
作者
Yanagisawa, Akira [1 ]
Ichikawa, Toshikazu
Arai, Takayoshi
机构
[1] Chiba Univ, Fac Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Grad Sch Sci & Technol, Inage Ku, Chiba 2638522, Japan
关键词
asymmetric catalysis; aldol reaction; tin alkoxide-1; BINAP; silver; alkenyl esters; aldehydes;
D O I
10.1016/j.jorganchem.2006.08.048
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A catalytic asymmetric aldol reaction of alkenyl trichloroacetates with aldehydes was achieved using dibutyltin dimethoxide and BINAP (.) silver(I) complex as catalysts in a mixed solvent consisting of THF and MeOH. Various optically active beta-hydroxy ketones were diastereoselectively obtained not only from aromatic and alpha,beta-unsaturated aldehydes but also from an aliphatic aldehyde with good enantioselectivity up to 92% ee. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:550 / 553
页数:4
相关论文
共 46 条
  • [11] Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
  • [12] The chemistry of trichlorosilyl enolates .2. Highly-selective asymmetric aldol additions of ketone enolates
    Denmark, SE
    Wong, KT
    Stavenger, RA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2333 - 2334
  • [13] Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects
    Denmark, SE
    Stavenger, RA
    Wong, KT
    Su, XP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 4982 - 4991
  • [14] Asymmetric catalysis with chiral Lewis bases
    Denmark, SE
    Stavenger, RA
    Su, XP
    Wong, KT
    Nishigaichi, Y
    [J]. PURE AND APPLIED CHEMISTRY, 1998, 70 (08) : 1469 - 1476
  • [15] Asymmetric catalysis of aldol reactions with chiral Lewis bases
    Denmark, SE
    Stavenger, RA
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 432 - 440
  • [16] Gennari C., 1991, COMPREHENSIVE ORGANI, V2, P629, DOI DOI 10.1016/B978-0-08-052349-1.00043-3
  • [17] Gröger H, 2001, ANGEW CHEM INT EDIT, V40, P529
  • [18] Groger H, 1998, CHEM-EUR J, V4, P1137
  • [19] Heathcock C. H., 1991, COMPREHENSIVE ORGANI, V2, P133, DOI [10.1016/B978-0-08-052349-1.00027-5, DOI 10.1016/B978-0-08-052349-1.00027-5]
  • [20] HOMOGENEOUS CATALYSIS - MECHANISMS OF THE CATALYTIC MUKAIYAMA ALDOL AND SAKURAI ALLYLATION REACTIONS
    HOLLIS, TK
    BOSNICH, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) : 4570 - 4581