A new stereoselective route to preparing optically active 2-imino-penam derivatives

被引:0
|
作者
Herak, JJ
Vinkovic, M
机构
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and simple procedure for preparation of (5R,6S)-2-benzylimino-6-bromo-3-isopropylidene-penam 2 and (5R,6S)-2-benzylimino-3-isopropylidene-penam 8 is described. The 2-imino-penam derivatives are prepared by modification of the Cooper reductive rearrangement of 3 alpha-benzylamide of penicillanic acid sulfoxides. The absolute configurations of starting sulfoxides and imino-products are assigned on the basis of H-1-NMR spectroscopic studies and verified by X-ray structure analysis of sulfoxide 3b and imino-penam 8.
引用
收藏
页码:1367 / 1376
页数:10
相关论文
共 50 条
  • [2] Two novel optically active penam derivatives
    Danilovski, A
    Vinkovic, M
    Herak, JJ
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 656 - 659
  • [3] Stereoselective reactions of optically active derivatives of α-methylbenzylaminophosphine
    Kolodyazhnyi, OI
    Andrushko, NV
    Grishkun, EV
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2004, 74 (04) : 515 - 522
  • [4] Stereoselective Reactions of Optically Active Derivatives of α-Methylbenzylaminophosphine
    O. I. Kolodyazhnyi
    N. V. Andrushko
    E. V. Grishkun
    Russian Journal of General Chemistry, 2004, 74 : 515 - 522
  • [5] En route to optically active ethynylglycine derivatives
    Meffre, P.
    Gauzy, L.
    Perdigues, C.
    Desanges-Levecque, F.
    Tetrahedron Letters, 36 (06):
  • [6] STEREOSELECTIVE HYDROLYSIS OF OPTICALLY-ACTIVE CHOLINE DERIVATIVES BY CHOLINESTERASES
    MOOSLER, A
    HASELMEYER, KH
    ZECH, R
    BIOLOGICAL CHEMISTRY HOPPE-SEYLER, 1988, 369 (09): : 879 - 880
  • [7] Stereoselective synthesis of optically active perhydrofuro[2,3-b]furan derivatives
    Uchiyama, M
    Hirai, M
    Nagata, M
    Katoh, R
    Ogawa, R
    Ohta, A
    TETRAHEDRON LETTERS, 2001, 42 (28) : 4653 - 4656
  • [8] New route to optically active building blocks
    不详
    CHEMICAL & ENGINEERING NEWS, 2002, 80 (33) : 35 - 35
  • [9] EN-ROUTE TO OPTICALLY-ACTIVE ETHYNYLGLYCINE DERIVATIVES
    MEFFRE, P
    GAUZY, L
    PERDIGUES, C
    DESANGESLEVECQUE, F
    BRANQUET, E
    DURAND, P
    LEGOFFIC, F
    TETRAHEDRON LETTERS, 1995, 36 (06) : 877 - 880
  • [10] A stereoselective carbohydrate route to optically active furo[2,3-b]benzofuran ring system
    Lakshmi, R
    Balasubramanian, KK
    ARKIVOC, 2003, : 140 - 145