Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

被引:10
作者
Kuznetsov, Nikolai Yu. [1 ]
Tikhov, Rabdan M. [1 ]
Strelkova, Tatiana V. [1 ]
Bubnov, Yuri N. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov 28, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
ASYMMETRIC-SYNTHESIS; ORGANOBORON COMPOUNDS; HOMOALLYLIC AMINES; ORGANOMETALLIC REAGENTS; CHIRAL SYNTHESIS; ALLYLBORATION; ALPHA; IMINES; ACIDS; ALCOHOLS;
D O I
10.1021/acs.orglett.8b01317
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triallylborane-amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman's imine was achieved with triallylborane-methylamine adduct.
引用
收藏
页码:3549 / 3552
页数:4
相关论文
共 56 条
  • [21] Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines
    Jiang, Liyin
    Cao, Peng
    Wang, Min
    Chen, Bin
    Wang, Bing
    Liao, Jian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (44) : 13854 - 13858
  • [22] Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols
    Jiang, Yao
    Schaus, Scott E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (06) : 1544 - 1548
  • [23] Jonnalagadda SC, 2016, ACS SYM SER, V1236, P67
  • [24] Kobayashi S., 2005, CHEM COMMUN, V104
  • [25] Synthesis of bridged azabicycles from isoquinolines via a tandem of allylboration and intramolecular metathesis
    Kuznetsov, N. Yu.
    Lyssenko, K. A.
    Peregudov, A. S.
    Bubnov, Yu. N.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2007, 56 (08) : 1569 - 1574
  • [26] A New Method of Synthesis of 6-Substituted Piperidine-2,4-diones from Homoallylamines
    Kuznetsov, Nikolai Yu.
    Maleev, Victor I.
    Khrustalev, Victor N.
    Mkrtchyan, Anna F.
    Godovikov, Ivan A.
    Strelkova, Tatyana V.
    Bubnov, Yuri N.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) : 334 - 344
  • [27] Lawrence S. A, 2004, AMINES SYNTHESIS PRO
  • [28] Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis
    Lee, Jin Hee
    Gupta, Sreya
    Jeong, Wook
    Rhee, Young Ho
    Park, Jaiwook
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) : 10851 - 10855
  • [29] Masao K., 1956, CHEM ABSTR, V50, Patent No. 7019
  • [30] Mikhailov B.M., 1961, B ACAD SCI USSR CH, V10, P1076