user

One-Pot Three-Component Catalytic Enantioselective Synthesis of Homoallylboronates

被引：80
|
作者：
Ibrahem, Ismail [1 ]
Breistein, Palle [1 ]
Cordova, Armando [1 ,2 ,3 ]
机构：
[1] Mid Sweden Univ, Dept Nat Sci Engn & Math, SE-85170 Sundsvall, Sweden
[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, Stockholm, Sweden
[3] Stockholm Univ, Berzelii Ctr EXSELENT, Stockholm, Sweden
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 50期
关键词：
asymmetric catalysis; boron; conjugate additions; multicomponent reactions; Wittig reactions; ASYMMETRIC ALLYLIC ALKYLATION; BORON CONJUGATE ADDITIONS; TRANSITION-METAL; MULTICOMPONENT REACTIONS; 1,6-CONJUGATE ADDITION; CASCADE CATALYSIS; BETA-BORATION; ALDEHYDES; HYDROBORATION; ESTERS;
D O I：
10.1002/anie.201105458
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
No longer a simple bor(ation): The title reaction between bis(pinacolato)diboron, enals, and 2-(triphenylphosphoranylidene)acetates employing bench-stable copper salts and a simple chiral amine co-catalyst is presented (see scheme). The reaction proceeds through a catalytic asymmetric conjugate borane addition/Wittig sequence wherein the β-boration step is 1,4-selective and gives the corresponding homoallylboronate products with high enantiomeric ratios. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：12036 / 12041
页数：6
相关论文
共 50 条
  • [21] A novel, one-pot and three-component synthesis of α-quinoxalinyl triphenylphosphoranes
    Adib, Mehdi
    Sheibani, Esmaeil
    Abbasi, Alireza
    Bijanzadeh, Hamid Reza
    TETRAHEDRON LETTERS, 2007, 48 (07) : 1179 - 1182
  • [22] Three-component one-pot reaction for the synthesis of β-amide ketones
    Yan-Ping Luo
    Qiong Chen
    Chemical Papers, 2013, 67 : 532 - 537
  • [23] One-pot three-component synthesis of α-amino phosphonate derivatives
    Heydari, Akbar
    Arefi, Afsaneh
    CATALYSIS COMMUNICATIONS, 2007, 8 (07) : 1023 - 1026
  • [24] One-Pot Three-Component Synthesis of Oxazine Derivatives in Water
    Rostami-Charati, Faramarz
    Hossaini, Zinatossadat
    Gharaee, Ebrahim
    Khalilzadeh, Mohammad A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 : E174 - E177
  • [25] One-Pot, Three-Component Coupling Approach to the Synthesis of α-Iminocarboxamides
    Masui, Hisashi
    Fuse, Shinichiro
    Takahashi, Takashi
    ORGANIC LETTERS, 2012, 14 (16) : 4090 - 4093
  • [26] Three-Component, One-Pot Synthesis of New Functionalized Pyrrolines
    Asghari, Sakineh
    Qandalee, Mohammad
    SYNTHETIC COMMUNICATIONS, 2010, 40 (14) : 2172 - 2177
  • [27] Highly enantioselective one-pot, three-component imino-reformatsky reaction
    Cozzi, PG
    Rivalta, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) : 3600 - 3603
  • [28] Ketones in the catalytic three-component “one-pot” Kabachnik-Fields synthesis of α-amino phosphonates
    E. D. Matveeva
    T. A. Podrugina
    M. V. Prisyajnoy
    N. S. Zefirov
    Russian Chemical Bulletin, 2006, 55 : 1209 - 1214
  • [29] Ketones in the catalytic three-component "one-pot" Kabachnik-Fields synthesis of α-amino phosphonates
    Matveeva, E. D.
    Podrugina, T. A.
    Prisyajnoy, M. V.
    Zefirov, N. S.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (07) : 1209 - 1214
  • [30] One-pot, three-component approach to diarylacetonitriles
    Singh, Dileep Kumar
    Prasad, Sure Siva
    Kim, Jinhwang
    Kim, Ikyon
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (05): : 669 - 673
12345