The progress in the chemistry of N-acyliminium ions and their use in stereoselective organic synthesis

被引:24
|
作者
Vinogradov, Maxim G. [1 ]
Turova, Olga V. [2 ]
Zlotin, Sergei G. [2 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Lab Fine Organ Synth, ZIOC RAS, Leninsky Prosp 47, Moscow 119991, Russia
[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Lab Fine Organ Synth, Leninsky Prosp 47, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
IN-SITU GENERATION; DIASTEREOSELECTIVE CONSTRUCTION; MANNICH REACTIONS; FACILE SYNTHESIS; CYCLIZATION; ACID; THIOUREA; INDOLES; ACCESS; DERIVATIVES;
D O I
10.1070/RCR4628
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The review summarizes data published in the last decade on the reactions of organic compounds involving N-acyliminium ions, including intramolecular arylation (cyclization), cross-coupling with nucleophiles and some other transformations to form new carbon carbon and carbon-heteroatom bonds. The stereo-and enantioselective versions of these reactions using chiral auxiliaries and asymmetric catalysts (organocatalysts) are considered. Examples of application of N-acyliminium ions for the synthesis of natural compounds and their analogues are presented. The bibliography includes 100 references.
引用
收藏
页码:1 / 17
页数:17
相关论文
共 50 条
  • [1] STEREOSELECTIVE ADDITION OF ORGANOCOPPER REAGENTS TO CYCLIC N-ACYLIMINIUM IONS
    LUDWIG, C
    WISTRAND, LG
    ACTA CHEMICA SCANDINAVICA, 1994, 48 (04): : 367 - 371
  • [2] Stereoselective Cycloaddition of N-Acyliminium Ions with α,β-Unsaturated Ketones and Esters
    Qian Lingfeng
    Zhou Yuehua
    Zhang Wei
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (03) : 449 - 456
  • [3] Cyclizations of N-acyliminium ions
    Maryanoff, BE
    Zhang, HC
    Cohen, JH
    Turchi, IJ
    Maryanoff, CA
    CHEMICAL REVIEWS, 2004, 104 (03) : 1431 - 1628
  • [4] New developments in the chemistry of N-acyliminium ions and related intermediates
    Speckamp, WN
    Moolenaar, MJ
    TETRAHEDRON, 2000, 56 (24) : 3817 - 3856
  • [5] THE SYNTHESIS OF (+/-)-SOLENOPSIN A AND (+/-)-DENDROPRIMINE - STEREOSELECTIVE REACTIONS OF 1,2-DIHYDROPYRIDINES AND N-ACYLIMINIUM IONS
    COMINS, DL
    WEGLARZ, MA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 23 - ORGN
  • [6] ABINITIO STUDIES ON N-ACYLIMINIUM IONS
    LAMATSCH, B
    SEEBACH, D
    HA, TK
    HELVETICA CHIMICA ACTA, 1992, 75 (04) : 1095 - 1110
  • [7] π-cyclization reactions of thio N-acyliminium ions for heterocyclic synthesis
    Sheehan, SM
    Beall, LS
    Padwa, A
    TETRAHEDRON LETTERS, 1998, 39 (27) : 4761 - 4764
  • [8] Stereoselective synthesis of trans-2,3-disubstituted pyrrolidines via addition to N-acyliminium ions
    Buezo, ND
    Jiménez, A
    Pedregal, C
    Vidal, P
    TETRAHEDRON LETTERS, 2006, 47 (15) : 2489 - 2492
  • [9] Synthesis of spirocyclic heterocycles from α,β-unsaturated N-acyliminium ions
    Thaima, Thanphat
    Yazici, Arife
    Auranwiwat, Chiramet
    Willis, Anthony C.
    Wille, Uta
    Limtharakul, Thunwadee
    Pyne, Stephen. G.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (01) : 259 - 272
  • [10] Application of N-acyliminium ions in the asymmetric synthesis of indole alkaloids
    Thomas, Christopher I.
    Allin, Steven M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231