Asymmetric Addition of Diethyl Zinc to Benzaldehyde Catalyzed by Chiral Diamine Ligand and Ti-diamine Modified Complex Derived from D-mannitol

被引:0
作者
Al Majid, Abdullah M. A. [1 ]
Al-Hazimi, Hassan M. A. [1 ]
Al-Shammery, Mohammed B. [2 ]
机构
[1] King Saud Univ, Fac Sci, Chem Dept, POB 2455, Riyadh 11451, Saudi Arabia
[2] Alkharj Univ, Fac Sci & Humanitarian Studies, Alkharj, Saudi Arabia
关键词
Diazide; Chiral diamine; Ttitanium complex; Diethyl zinc; Benzaldehyde; Asymmetric; Enantioselectivity; Addition;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Modified procedure for preparation of chiral: 3,4-Diazido-1, 2:5, 6-di-O-isopropylidene-Dmannitol from the corresponding bismesylate and new chiral ligand: 3, 4-diamino-1, 2:5, 6-Oisopropylidene-D-mannitol was described. The application of both diamine and Ti-diamine complex as catalysts in enantioselective addition of diethyl zinc to prochiral benzaldehyde was described. High enantioselectivity up to 93% e.e. was achieved. The standard analytical measurements including optical activity of the diazide, diamine and the determination of optical purity of the resulting alcohol were reported. [GRAPHICS]
引用
收藏
页码:221 / 230
页数:10
相关论文
共 37 条
  • [31] Radical reactions in aqueous medium using (Me3Si)3SiH
    Postigo, Al
    Kopsov, Sergey
    Ferreri, Carla
    Chatgilialoglu, Chryssostornos
    [J]. ORGANIC LETTERS, 2007, 9 (25) : 5159 - 5162
  • [32] PROCTER G, 1999, ASYMMETRIC SYNTHESIS
  • [33] A novel, simple, chemoselective and practical protocol for the reduction of azides using In/NH4Cl
    Reddy, GV
    Rao, GV
    Iyengar, DS
    [J]. TETRAHEDRON LETTERS, 1999, 40 (20) : 3937 - 3938
  • [34] SYNTHESIS OF 2,3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE IN HIGH CHEMICAL AND OPTICAL PURITY - OBSERVATIONS ON THE DEVELOPMENT OF A PRACTICAL BULK PROCESS
    SCHMID, CR
    BRYANT, JD
    DOWLATZEDAH, M
    PHILLIPS, JL
    PRATHER, DE
    SCHANTZ, RD
    SEAR, NL
    VIANCO, CS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) : 4056 - 4058
  • [35] Takahashi H., 1989, TETRAHEDRON LETT, V30, P1657
  • [36] Production of D-mannitol by heterofermentative lactic acid bacteria
    von Weymarn, N
    Hujanen, M
    Leisola, M
    [J]. PROCESS BIOCHEMISTRY, 2002, 37 (11) : 1207 - 1213
  • [37] Preparation of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene from two versatile 1,3,5-tri(halosubstituted) 2,4,6-triethylbenzene derivatives
    Wallace, KJ
    Hanes, R
    Anslyn, E
    Morey, J
    Kilway, KV
    Siegel, J
    [J]. SYNTHESIS-STUTTGART, 2005, (12): : 2080 - 2083