Synthesis of enantiomerically pure bicyclic lactams

被引:0
|
作者
Diedrichs, N [1 ]
Westermann, B [1 ]
机构
[1] Univ Gesamthsch Paderborn, Fachbereich chem & Chem Tech, D-33095 Paderborn, Germany
关键词
Grubbs' catalyst; ring-closing olefin metathesis; PLE; lactams; natural products;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically pure homologous 1-azabicyclo[x.y.0]alkanones (x = 4-5, y = 4-7) can be synthesized by ring closing olefin metathesis using Grubbs' ruthenium catalyst. By starting from monocyclic lactams, the bicyclic products, even eight- and nine-membered rings, are formed in high yields. The monocyclic lactames can be obtained enantiomerically pure by enzyme-catalyzed kinetic resolution.
引用
收藏
页码:1127 / 1129
页数:3
相关论文
共 50 条
  • [21] A novel stereocontrolled synthesis of enantiopure bicyclic lactams
    Agami, C
    Dechoux, L
    Hebbe, S
    TETRAHEDRON LETTERS, 2003, 44 (28) : 5311 - 5313
  • [22] Polymer-supported synthesis of bicyclic γ-lactams
    Zhu, T
    Yan, Z
    Chucholowski, A
    Li, RS
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (04): : 520 - 522
  • [23] Synthesis of allylamines in enantiomerically pure form
    Concellón, JM
    Baragaña, B
    Riego, E
    TETRAHEDRON LETTERS, 2000, 41 (22) : 4361 - 4362
  • [24] A convergent strategy for the asymmetric synthesis of enantiomerically pure bicyclic compounds by using a silicon-directed cycloaddition reaction: The synthesis of enantiomerically pure bicyclo[3.2.0]hept-2-en-6-one
    Adam, JM
    Ghosez, L
    Houk, KN
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (18) : 2728 - 2730
  • [25] Synthesis of enantiomerically pure δ-benzylproline derivatives
    Rodriguez, Isabel
    Isabel Calaza, M.
    Jimenez, Ana I.
    Cativiela, Carlos
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (05) : 3310 - 3318
  • [26] SYNTHESIS OF ENANTIOMERICALLY PURE LYSOPHOSPHATIDYLINOSITOLS AND ALKYLPHOSPHOINOSITOLS
    FILTHUTH, E
    EIBL, H
    CHEMISTRY AND PHYSICS OF LIPIDS, 1992, 60 (03) : 253 - 261
  • [27] Total Synthesis of Enantiomerically Pure (-)-Balanol
    Chimia Chemie Rep, 11 (530):
  • [28] An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary
    Joshi, SN
    Deshmukh, ARAS
    Bhawal, BM
    TETRAHEDRON-ASYMMETRY, 2000, 11 (07) : 1477 - 1485
  • [29] Synthesis of Enantiomerically Pure Oxiranylboronic Esters
    Fernandez, Enrique
    Frey, Wolfgang
    Pietruszka, Joerg
    SYNLETT, 2010, (09) : 1386 - 1388
  • [30] Efficient synthesis of enantiomerically pure dihydropyrans
    Hong, BC
    Chen, ZY
    Nagarajan, A
    Rudresha, K
    Chavan, V
    Chen, WH
    Jiang, YF
    Zhang, SC
    Lee, GH
    Sarshar, S
    TETRAHEDRON LETTERS, 2005, 46 (08) : 1281 - 1285