A highly stereoselective synthesis of indolyl N-substituted glycines

被引:53
|
作者
Jiang, B
Yang, CG
Gu, XH
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] Harvard Univ, McLean Hosp, Sch Med, Alcohol & Drug Abuse Res Ctr, Belmont, MA 02478 USA
关键词
indolyl boronic acid; indolylglycine; stereoselectivity;
D O I
10.1016/S0040-4039(01)00229-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active alpha -indolyl N-substituted glycines were synthesized by reaction of an indolyl boronic acid with glyoxylic acid using chiral methylbenzylamine as the chiral auxiliary with high diastereoselectivity. The absolute configuration of the product was determined by a single-crystal X-ray analysis. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2545 / 2547
页数:3
相关论文
共 50 条
  • [11] Chiral N-substituted glycines can form stable helical conformations
    Armand, P
    Kirshenbaum, K
    Falicov, A
    Dunbrack, RL
    Dill, KA
    Zuckermann, RN
    Cohen, FE
    FOLDING & DESIGN, 1997, 2 (06): : 369 - 375
  • [12] SYNTHESIS OF N-SUBSTITUTED METHANEDISULFONAMIDES AND N'-SUBSTITUTED METHANEDISULFONYLUREAS
    KESSLER, WV
    JENKINS, GL
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1961, 50 (10) : 842 - &
  • [13] SYNTHESIS OF N-SUBSTITUTED TRIMETHYLENEIMINES
    LEDINA, LE
    PERCHENKO, VN
    NAMETKIN, NS
    KRAPIVIN, AM
    DOKLADY AKADEMII NAUK SSSR, 1978, 243 (05): : 1200 - 1203
  • [14] THE SYNTHESIS OF N-SUBSTITUTED CARBAMATES
    SHRINER, RL
    CHILD, RG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (02) : 549 - 550
  • [15] SYNTHESIS OF N-SUBSTITUTED THIOUREA
    MOZOLIS, VV
    IOKUBAIT.SP
    USPEKHI KHIMII, 1973, 42 (07) : 1310 - 1324
  • [16] SYNTHESIS OF N-SUBSTITUTED ISOINDOLINES
    CHIMENTI, F
    VOMERO, S
    FARMACO-EDIZIONE SCIENTIFICA, 1975, 30 (11): : 884 - 890
  • [17] N-SUBSTITUTED GLYCINES AS REPLACEMENTS FOR PROLINE IN TRIPEPTIDE ALDEHYDE THROMBIN INHIBITORS
    SCHACHT, AL
    WILEY, MR
    CHIRGADZE, N
    CLAWSON, D
    CRAFT, TJ
    COFFMAN, WJ
    JONES, ND
    GIFFORDMOORE, D
    OLKOWSKI, J
    SHUMAN, RT
    SMITH, GF
    WEIR, LC
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (21) : 2529 - 2534
  • [18] Synthesis of N-substituted aminomethylenediphenylphosphinoxides
    Frolovskii, VA
    Studnev, YN
    Rozantsev, GG
    ZHURNAL OBSHCHEI KHIMII, 1996, 66 (04): : 692 - 693
  • [19] Synthesis of N-Substituted Malonodiimidates
    V. E. Shishkin
    Yu. V. Popov
    O. V. Anishchenko
    M. A. Shevchenko
    I. A. Kosheleva
    N. A. Sokolov
    Russian Journal of General Chemistry, 2018, 88 : 2200 - 2203
  • [20] Synthesis of N-Substituted Malonodiimidates
    Shishkin, V. E.
    Popov, Yu. V.
    Anishchenko, O. V.
    Shevchenko, M. A.
    Kosheleva, I. A.
    Sokolov, N. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (10) : 2200 - 2203