Design and synthesis of oxacycles from norbornene derivatives via ring-opening metathesis and ring-rearrangement metathesis

被引:10
|
作者
Kotha, Sambasivarao [1 ]
Ravikumar, Ongolu [1 ]
Sreevani, Gaddamedi [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Powai, India
关键词
Ring-rearrangement metathesis; Spirocycles; Oxacycles; Norbornene derivatives; DIELS-ALDER REACTION; DIVERSITY-ORIENTED APPROACH; ENYNE METATHESIS; RUTHENIUM; OXA; HETEROCYCLES; MECHANISM; LACTAM; BOWLS;
D O I
10.1016/j.tet.2016.08.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Norbornene derivatives containing oxygen atom(s) are found to undergo ring-rearrangement metathesis sequence to deliver cyclic ethers. Here, we have established a simple, efficient and an atom-economic process for the synthesis of fused and spiro-oxacyclic compounds starting with cyclopentadiene. Compounds prepared in this study are difficult to assemble by conventional retrosynthetic routes. (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码:6611 / 6615
页数:5
相关论文
共 50 条
  • [1] Application of Sequential Ring-Opening, and Ring-Closing Metathesis or Ring-Rearrangement Metathesis to Design Oxacycles and Azacycles
    Kotha, Sambasivarao
    Fatma, Ambareen
    CHEMISTRYSELECT, 2021, 6 (43): : 12018 - 12021
  • [2] Synthetic Approach to Oxacycles via the Application of Ring-Rearrangement Metathesis
    Kotha, Sambasivarao
    Fatma, Ambareen
    CHEMISTRYSELECT, 2021, 6 (31): : 7919 - 7921
  • [3] Ring-rearrangement metathesis
    Holub, Nicole
    Blechert, Siegfried
    CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (09) : 1064 - 1082
  • [4] LIVING RING-OPENING METATHESIS POLYMERIZATION OF MESOGENIC NORBORNENE DERIVATIVES
    PUGH, C
    MACROMOLECULAR SYMPOSIA, 1994, 77 : 325 - 337
  • [5] Diastereoselective ring-rearrangement metathesis
    Böhrsch, V
    Neidhöfer, J
    Blechert, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) : 1302 - 1305
  • [6] Ring-Rearrangement Metathesis of Cyclopropenes: Synthesis of Heterocycles
    Miege, Frederic
    Meyer, Christophe
    Cossy, Janine
    ORGANIC LETTERS, 2010, 12 (02) : 248 - 251
  • [7] Application of ring-rearrangement metathesis in organic synthesis: A grand design
    Kotha, Sambasivarao
    Meshram, Milind
    Aswar, Vikas R.
    TETRAHEDRON LETTERS, 2019, 60 (50)
  • [8] Advances in the study on ring-opening metathesis polymerization of norbornene and its derivatives
    Zhang, Danfeng
    Gaofenzi Cailiao Kexue Yu Gongcheng/Polymeric Materials Science and Engineering, 2000, 16 (01): : 13 - 15
  • [9] Ring-rearrangement metathesis of bicyclic amino acid derivatives
    Maechling, S
    Norman, SE
    McKendrick, JE
    Basra, S
    Köppner, K
    Blechert, S
    TETRAHEDRON LETTERS, 2006, 47 (02) : 189 - 192
  • [10] THE MECHANISM OF STEREOSELECTIVE RING-OPENING METATHESIS POLYMERIZATION OF NORBORNENE AND SEVERAL DERIVATIVES
    GILLAN, EMD
    HAMILTON, JG
    MACKEY, OND
    ROONEY, JJ
    JOURNAL OF MOLECULAR CATALYSIS, 1988, 46 (1-3): : 359 - 371