Synthesis of γ-fluoroalicylated allylic amine derivatives via palladium-catalyzed Overman rearrangement

被引：4
|
作者：
Jiang, Xin-Yi [1 ]
Chu, Lingling [1 ]
Wang, Ruo-Wen [1 ]
Qing, Feng-Ling [1 ,2 ]
机构：
[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 50期
基金：
中国国家自然科学基金;
关键词：
gamma-Fluoroalicylated allylic amines; Palladium-catalyzed; Overman rearrangement; ASYMMETRIC REARRANGEMENT; REGIOSELECTIVE SYNTHESIS; 1,3 TRANSPOSITION; AMINATION; ALCOHOL; PALLADACYCLES; ANALOGS; ESTERS;
D O I：
10.1016/j.tetlet.2012.10.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd-catalyzed Overman rearrangement of alpha-fluoroalkylated allylic trichloroacetimidates has been developed. This reaction allows for an efficient synthesis of gamma-fluoroalkylated allylic amine derivatives with excellent regio- and stereo-selectivities under mild conditions. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6853 / 6857
页数：5
相关论文
共 50 条
  • [1] PALLADIUM-CATALYZED REACTIONS OF VINYLIC BROMIDES WITH ALLYLIC ALCOHOL AND AMINE DERIVATIVES
    KAO, LC
    STAKEM, FG
    PATEL, BA
    HECK, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07): : 1267 - 1277
  • [2] Extending the substrate scope of palladium-catalyzed arylfluorination of allylic amine derivatives
    Novak, Tamas T.
    Nguyen, Thi Cam Tu
    Gomory, Agnes
    Hornyanszky, Gabor
    Remete, Attila Mario
    Kiss, Lorand
    JOURNAL OF FLUORINE CHEMISTRY, 2024, 273
  • [3] Palladium-catalyzed rearrangement of allylic sulfoximines: Application to the asymmetric synthesis of chiral allylic amines
    Pyne, SG
    Dong, ZM
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16): : 5517 - 5522
  • [4] Palladium-Catalyzed Synthesis of Allylic Ureas via an Isocyanate Intermediate
    Jay, Lucien P.
    Barker, Timothy J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (10) : 1829 - 1831
  • [5] Synthesis of cyclopentenones via intramolecular HWE and the palladium-catalyzed reactions of allylic hydroxy phosphonate derivatives
    Yan, Bingli
    Spilling, Christopher D.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5385 - 5396
  • [6] CYCLIZATIONS VIA PALLADIUM-CATALYZED ALLYLIC ALKYLATIONS
    TROST, BM
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09): : 1173 - 1192
  • [7] TERPENOID SYNTHESIS VIA PALLADIUM-CATALYZED ALLYLIC ALKYLATION OF ALLYLIC NITRO-COMPOUNDS
    ONO, N
    HAMAMOTO, I
    KAJI, A
    SYNTHESIS-STUTTGART, 1985, (10): : 950 - 952
  • [8] SYNTHESIS OF ALLYLIC ARYL ETHERS VIA PALLADIUM-CATALYZED DECARBOXYLATION OF ALLYLIC ARYL CARBONATES
    LAROCK, RC
    LEE, NH
    TETRAHEDRON LETTERS, 1991, 32 (44) : 6315 - 6318
  • [9] Synthesis of Fluorescent Amino Acids via Palladium-Catalyzed Allylic Alkylations
    Schmidt, Lisa
    Doroshenko, Tamara
    Barbie, Philipp
    Grueter, Andreas
    Jung, Gregor
    Kazmaier, Uli
    SYNTHESIS-STUTTGART, 2016, 48 (18): : 3077 - 3086
  • [10] Asymmetric Synthesis of (-)-Aurantioclavine via Palladium-Catalyzed Intramolecular Allylic Amination
    Suetsugu, Satoshi
    Nishiguchi, Hiromi
    Tsukano, Chihiro
    Takemoto, Yoshiji
    ORGANIC LETTERS, 2014, 16 (03) : 996 - 999
12345