Regio- and Stereoselective Copper-Catalyzed Ring Opening of Diheterobicyclic Alkenes with Grignard Reagents

被引：2
|
作者：
Crotti, Stefano [1 ]
Di Bussolo, Valeria [1 ]
Pineschi, Mauro [1 ]
机构：
[1] Univ Pisa, Dipartimento Sci Farmaceut, I-56126 Pisa, Italy
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 10期
关键词：
fused ring systems; cycloadducts; copper catalysis; Grignard reagents; regioselectivity; stereoselectivity; MESO-BICYCLIC HYDRAZINES; OXABICYCLIC ALKENES; DESYMMETRIZATION; CYCLOADDUCTS; STRATEGY;
D O I：
10.1055/s-0031-1290821
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The ring opening of bicyclic hydrazines and bicyclic oxazines with organomagnesium reagents under the influence of copper catalysts allows functionalized cyclopentene and cyclohexene derivatives to be obtained. Whereas complete anti-stereoselective ring opening occurred in all cases, the regioselective outcome turned out to be highly dependent on the reaction conditions used.
引用
收藏
页码：1511 / 1514
页数：4
相关论文
共 50 条
  • [1] Copper-Catalyzed Regio- and Stereoselective Ring-Opening of Cyclic Sulfamidates with Grignard Reagents assisted by Lithium Chloride
    Arigala, Pitchaiah
    Sadu, Venkata S.
    Hwang, In-Taek
    Hwang, Jin-Soo
    Kim, Chul-Ung
    Lee, Kee-In
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2027 - 2032
  • [2] Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with grignard reagents
    Zhang, W
    Wang, LX
    Shi, WJ
    Zhou, QL
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09): : 3734 - 3736
  • [3] Highly Enantioselective Copper-Catalyzed Ring Opening of Oxabicyclic Alkenes with Grignard Reagents
    Zhang, Wei
    Zhu, Shou-Fei
    Qiao, Xiang-Chen
    Zhou, Qi-Lin
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (12) : 2105 - 2111
  • [4] Copper-Catalyzed Regio- and Enantioselective Addition of Silicon Grignard Reagents to Alkenes Activated by Azaaryl Groups
    Mao, Wenbin
    Xue, Weichao
    Irran, Elisabeth
    Oestreich, Martin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (31) : 10723 - 10726
  • [5] Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with Grignard reagents
    Arrayás, RG
    Cabrera, S
    Carretero, JC
    ORGANIC LETTERS, 2003, 5 (08) : 1333 - 1336
  • [6] Copper-catalyzed anti-stereocontrolled ring-opening of azabicyclic alkenes with grignard reagents
    Arrayás, RG
    Cabrera, S
    Carretero, JC
    ORGANIC LETTERS, 2005, 7 (02) : 219 - 221
  • [7] Iron-catalyzed regio- and stereoselective ring opening of [2.2.1]- and [3-2.1]oxabicyclic alkenes with a Grignard reagent
    Nakamura, M
    Matsuo, K
    Inoue, T
    Nakamura, E
    ORGANIC LETTERS, 2003, 5 (08) : 1373 - 1375
  • [8] Copper-Catalyzed Regio- and Stereoselective Hydroarylation of Ynamide
    Maity, Avijit
    Sahoo, Akhila K.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 852 - 863
  • [9] Copper-Catalyzed Regio- and Stereoselective Aminoboration of Alkenylboronates
    Nishikawa, Daiki
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2016, 18 (19) : 4856 - 4859
  • [10] Copper-catalyzed regio- and stereoselective fluorocarboalkynylation of alkynes
    Zhao, Binlin
    Zheng, Yukun
    Zhu, Tianxiang
    Wang, Mengning
    Wang, Minyan
    Ma, Mengtao
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6857 - 6862
12345