Palladium-Catalyzed Ring Opening of Aminocyclopropyl Ugi Adducts

被引:12
|
作者
Dos Santos, Aurelie [1 ]
El Kaim, Laurent [1 ]
Grimaud, Laurence [1 ]
Ramozzi, Romain [1 ]
机构
[1] Ecole Natl Super Tech Avancees, UMR 7652, Lab DCSO ENSTA Polytech CNRS, F-75739 Paris 15, France
关键词
aminocyclopropanes; ring opening; palladium; Ugi; Ugi-Smiles; ORGANIC-SYNTHESIS; MULTICOMPONENT REACTIONS; 3+2 CYCLOADDITIONS; CYCLOPROPANES; DERIVATIVES; CHEMISTRY; METHYLENECYCLOPROPANES; SILOXYCYCLOPROPANES; REARRANGEMENTS; CYCLIZATION;
D O I
10.1055/s-0031-1290312
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring opening of aminocyclopropanes triggered by activation with an intramolecular arylpalladium(II) iodide complex is an interesting strategy for the synthesis of nitrogen heterocycles and a valuable Ugi postcondensation-type transformation. Six- and seven-membered-ring cyclic enamines may be obtained.
引用
收藏
页码:438 / 442
页数:5
相关论文
共 50 条
  • [21] Palladium-catalyzed ring-opening reaction of methyleneaziridines with carboxylic acids:: Synthesis of α-amidoketones
    Oh, YH
    Nakamura, I
    Yamamoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08): : 2856 - 2858
  • [22] Palladium-Catalyzed syn-Stereocontrolled Ring Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides
    Chen, Donghan
    Yao, Yongqi
    Yang, Wen
    Lin, Qifu
    Li, Huanyong
    Wang, Lin
    Chen, Shuqi
    Tang, Yun
    Yang, Dingqiao
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (19): : 12481 - 12489
  • [23] Palladium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Potassium Trifluoroborate Salts
    Tao, Pingfang
    Huang, Jun
    Liu, Yuzhao
    Wei, Guangming
    Wang, Yifei
    Wei, Xiansheng
    Huang, Guobao
    Li, Xiuying
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1630 - 1637
  • [24] Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes
    Tan, Yun
    Yao, Yongqi
    Yang, Wen
    Lin, Qifu
    Huang, Guobao
    Tan, Minxiong
    Chen, Shuqi
    Chen, Donghan
    Yang, Dingqiao
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 139 - 145
  • [25] Palladium-catalyzed ring opening of 5-vinyloxazolidinones. Synthesis and utility of vinyloxazolines.
    Cook, GR
    Shanker, PS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U44 - U44
  • [26] Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols
    Tait, Katrina
    Alrifai, Oday
    Boutin, Rebecca
    Haner, Jamie
    Tam, William
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 2189 - 2196
  • [27] Ring opening in the hydroamination of methylenecyclopropanes catalyzed by palladium
    Nakamura, I
    Itagaki, H
    Yamamoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19): : 6458 - 6459
  • [28] Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C1-Tethered Aryl Halides
    Koh, Samuel
    Pounder, Austin
    Brown, Elizabeth
    Tam, William
    ORGANIC LETTERS, 2020, 22 (09) : 3433 - 3437
  • [29] Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates
    Li, Yue
    Yang, Wen
    Cheng, Guo
    Yang, Dingqiao
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4744 - 4750
  • [30] Palladium-catalyzed stereocontrolled ring-opening of 7-oxabenzonorbornadienes with organic carboxylic acids
    Saravanan, Velautham
    Jeganmohan, Masilamani
    CHEMICAL COMMUNICATIONS, 2023, 59 (37) : 5619 - 5622