Synthesis of enantiopure angularly condensed [2.2]paracyclophanes containing five-membered rings

被引：20
|
作者：
Minuti, L
Taticchi, A
Marrocchi, A
Lanari, D
Broggi, A
Gacs-Baitz, E
机构：
[1] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy
[2] Hungarian Acad Sci, Cent Inst Chem, H-1525 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 04期
关键词：
D O I：
10.1016/S0957-4166(02)00833-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Optically active angularly condensed [2.2]paracyclophanes containing five-membered rings hake been synthesized by a two-step approach based on the Diels-Alder cycloaddition of (S)-(+)-4-vinyl[2.2]paracyclophane. Structural analysis by NMR spectroscopy is presented. These helicenophanes containing a cyclopentane ring show extraordinarily high specific rotations. This phenomenon has been discussed in terms of structural modifications caused by the replacement of the benzene unit with a cyclopentane ring. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：481 / 487
页数：7
相关论文
共 50 条
  • [41] Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings
    Zhang, B
    Lash, TD
    TETRAHEDRON LETTERS, 2003, 44 (39) : 7253 - 7256
  • [42] Predicting the photoresponse of soot nuclei: Spectroscopic characteristics of aromatic aggregates containing five-membered rings
    Krueger, Rachel A.
    Blanquart, Guillaume
    COMBUSTION AND FLAME, 2020, 217 (217) : 85 - 92
  • [43] 1,3-dipolar Cycloadditions Involving Allenes: Synthesis of Five-membered Rings
    Cardoso, Ana L.
    Soares, Maria I. L.
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (27) : 3064 - 3134
  • [44] Conducting complexes of TTF and TSF derivatives fused with selenium-containing five-membered rings
    Jigami, T.
    Takimiya, K.
    Aso, Y.
    Otsubo, T.
    Synthetic Metals, 1999, 102 (1 -3 pt 2): : 1714 - 1715
  • [45] Conducting complexes of TTF and TSF derivatives fused with selenium-containing five-membered rings
    Jigami, T
    Takimiya, K
    Aso, Y
    Otsubo, T
    SYNTHETIC METALS, 1999, 102 (1-3) : 1714 - 1715
  • [46] Photochemistry of diethynyl sulfides: A cycloaromatization for the formation of five-membered rings
    Lewis, KD
    Wenzler, DL
    Matzger, AJ
    ORGANIC LETTERS, 2003, 5 (13) : 2195 - 2197
  • [47] PREPARATION OF ACYLHETEROCUMULENES FROM FIVE-MEMBERED RINGS WITH AID OF PHOSPHINES
    GOERDELER, J
    HAAG, J
    LINDNER, C
    LOSCH, R
    CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (02): : 502 - 507
  • [48] Gold and silver assisted synthesis of five-membered oxygen and nitrogen containing heterocycles
    Kaur, Navjeet
    SYNTHETIC COMMUNICATIONS, 2019, 49 (12) : 1459 - 1485
  • [49] SOLID-PHASE SYNTHESIS OF NITROGEN-CONTAINING FIVE-MEMBERED HETEROCYCLES
    Kaur, Navjeet
    Dwivedi, Jaya
    Kishore, Dharma
    SYNTHETIC COMMUNICATIONS, 2014, 44 (12) : 1671 - 1729
  • [50] Synthesis of Five-Membered Heterocycles Containing Nitrogen Heteroatom Under Ultrasonic Irradiation
    Kaur, Navjeet
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2019, 16 (05) : 481 - 503
12345