Titanium-mediated synthesis of bicyclic cyclopropylamines from unsaturated nitriles

被引：37
|
作者：
Laroche, C [1 ]
Bertus, P [1 ]
Szymoniak, J [1 ]
机构：
[1] Univ Reims, CNRS, UMR 6519 React Select & Applicat, UFR Sci, F-51687 Reims 2, France
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 12期
关键词：
bicyclic compounds; cyclizations; cyclopropanes; nitriles; titanium;
D O I：
10.1016/S0040-4039(03)00325-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Here we report an easy synthesis of bicyclic primary cyclopropylamines directly from unsaturated nitriles. The described reaction involves Ti(II)-mediated intramolecular coupling of alkene and nitrile moieties. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2485 / 2487
页数：3
相关论文
共 50 条
  • [1] Titanium-mediated synthesis of primary cyclopropylamines from nitriles and Grignard reagents
    Bertus, Philippe
    Szymoniak, Jan
    SYNLETT, 2007, (09) : 1346 - 1356
  • [2] Titanium-mediated syntheses of cyclopropylamines
    de Meijere, A
    Kozhushkov, SI
    Savchenko, AI
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (12) : 2033 - 2055
  • [3] Titanium-Mediated Cyclopropanation of Nitriles with Unsaturated Grignard Reagents: Application to the Synthesis of Constrained Lysine Derivatives
    Forcher, Gwenael
    Clousier, Nathalie
    Beauseigneur, Alice
    Setzer, Paul
    Boeda, Fabien
    Pearson-Long, Morwenna S. M.
    Karoyan, Philippe
    Szymoniak, Jan
    Bertus, Philippe
    SYNTHESIS-STUTTGART, 2015, 47 (07): : 992 - 1006
  • [4] Titanium-mediated synthesis of substituted cyclobutanes
    Alleyn, James
    Bradley, Jillian
    Walker, Renee
    Perez, Felix
    Gesinski, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [5] TITANIUM-MEDIATED SYNTHESIS OF CONJUGATED DIENES
    DOXSEE, KM
    MOUSER, JKM
    TETRAHEDRON LETTERS, 1991, 32 (14) : 1687 - 1690
  • [6] Synthesis of bicyclic cyclopropylamines from amino acid derivatives
    Faler, CA
    Cao, B
    Joullié, MM
    HETEROCYCLES, 2006, 67 (02) : 519 - +
  • [7] NEW TITANIUM-MEDIATED CYCLIZATION REACTIONS FOR THE SYNTHESIS OF E,E-EXOCYCLIC DIENES AND OF BICYCLIC ENONES
    NUGENT, WA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 328 - INR
  • [8] Titanium-mediated olefination reactions for the synthesis of allenes and cumulenes
    Petasis, Nicos A.
    Arden, Charles
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [9] Synthesis of secondary amines by titanium-mediated transfer of alkenyl groups from alcohols
    Ramanathan, Balasubramanian
    Odom, Aaron L.
    Journal of the American Chemical Society, 2006, 128 (29): : 9344 - 9345
  • [10] TITANIUM-MEDIATED SYNTHESIS OF VICINAL GLYCOLS FROM CARBOXYLIC ACIDS AND ORGANOLITHIUM COMPOUNDS
    AXELROD, EH
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (07): : 451 - &
12345