Lewis Acid Catalyzed SN2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes

被引:53
|
作者
Ghorai, Manas K. [1 ]
Tiwari, Deo Prakash [1 ]
Jain, Nikita [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 14期
关键词
ENANTIOSELECTIVE SYNTHESIS; MESO-AZIRIDINES; C-ARYLATION; STEREOCONTROLLED SYNTHESIS; CYCLIZATION REACTIONS; EFFICIENT CATALYST; TOSYL AZIRIDINES; SYNTHETIC ROUTE; DERIVATIVES; TRANSFORMATION;
D O I
10.1021/jo401028j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient Lewis acid catalyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to provide substituted 2,2-diaryl/heteroarylethylamines in excellent yields and stereoselectivity (er, dr >99:1) is described.
引用
收藏
页码:7121 / 7130
页数:10
相关论文
共 32 条
  • [21] Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones:: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols
    Ghorai, Manas K.
    Das, Kalpataru
    Kumar, Amit
    TETRAHEDRON LETTERS, 2007, 48 (25) : 4373 - 4377
  • [22] BF3·OEt2 catalyzed base-free regiospecific ring opening of N-activated azetidines with (E)-1-arylidene-2-arylhydrazines
    Ranadeep Talukdar
    Journal of the Iranian Chemical Society, 2019, 16 : 127 - 136
  • [23] BF3•OEt2 catalyzed base-free regiospecific ring opening of N-activated azetidines with (E)-1-arylidene-2-arylhydrazines
    Talukdar, Ranadeep
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (01) : 127 - 136
  • [24] A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N Cyclization
    Sayyad, Masthanvali
    Mal, Abhijit
    Wani, Imtiyaz Ahmad
    Ghorai, Manas K.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6424 - 6432
  • [25] Methanesulfonic Acid Catalyzed Friedel-Crafts Reaction of Electron-Rich Arenes with N-Arylmaleimides: A Highly Efficient Metal-Free Route To Access 3-Arylsuccinimides
    Gairola, Deepti
    Peddinti, Rama Krishna
    SYNTHESIS-STUTTGART, 2021, 53 (11): : 1923 - 1930
  • [26] One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines
    Crespin, Lorene
    Biancalana, Lorenzo
    Morack, Tobias
    Blakemore, David C.
    Ley, Steven V.
    ORGANIC LETTERS, 2017, 19 (05) : 1084 - 1087
  • [27] REACTIONS WITH AZIRIDINES .55. N-S CLEAVAGE IS FASTER THAN HOMOLYTIC RING-OPENING IN SINGLE-ELECTRON TRANSFER TO SOME N-SULFONYLAZIRIDINES - COMPETITION BETWEEN SN2 AND SET
    BELLOS, K
    STAMM, H
    SPETH, D
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24): : 6846 - 6849
  • [28] Friedel-Crafts Arylation Reactions of N-Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl3•6H2O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes
    Thirupathi, Ponnaboina
    Kim, Sung Soo
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5240 - 5249
  • [29] A practical approach to non-natural or N-unsubstituted α-arylglycine derivatives:: Hf(OTf)4-doped Me3SiCl system-catalyzed aminomethylation of electron-rich arenes with a new type of N,O-acetal
    Sakai, Norio
    Asano, Junichi
    Shimano, Yuta
    Onakahara, Takeo
    TETRAHEDRON, 2008, 64 (39) : 9208 - 9215
  • [30] Schottky Barrier Induced Coupled Interface of Electron-Rich N-Doped Carbon and Electron-Deficient Cu: In-Built Lewis Acid-Base Pairs for Highly Efficient CO2 Fixation
    Liu, Yong-Xing
    Wang, Hong-Hui
    Zhao, Tian-Jian
    Zhang, Bing
    Su, Hui
    Xue, Zhong-Hua
    Li, Xin-Hao
    Chen, Jie-Sheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) : 38 - 41