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
  • [41] InBr3-catalyzed three-component, one-pot synthesis of imidazo[1,2-a]pyridines
    Reddy, B. V. Subba
    Reddy, P. Sivaramakrishna
    Reddy, Y. Jayasudhan
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2011, 52 (44) : 5789 - 5793
  • [42] One-pot, three-component synthesis of open-chain, polyfunctional sulfones
    Bouchez, Laure
    Vogel, Pierre
    Synthesis, 2002, (02) : 225 - 231
  • [43] Exploiting the Divergent Reactivity of Isocyanoacetates: One-Pot Three-Component Synthesis of Functionalized Angular Furoquinolines
    Bouma, Marinus J.
    Masson, Geraldine
    Zhu, Jieping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (03) : 475 - 479
  • [44] An efficient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives
    Sable, Pravinkumar N.
    Ganguly, Swastika
    Chaudhari, Pravin D.
    CHINESE CHEMICAL LETTERS, 2014, 25 (07) : 1099 - 1103
  • [45] Meglumine catalyzed one-pot, three-component combinatorial synthesis of pyrazoles bearing a coumarin unit
    Li, Xiao-Tang
    Liu, Yu-Heng
    Liu, Xin
    Zhang, Zhan-Hui
    RSC ADVANCES, 2015, 5 (33): : 25625 - 25633
  • [46] Three-component one-pot synthesis of functionalised (Z)-4-benzylidene (and alkenylidene) pyrrolidines
    Azoulay, S
    Monteiro, N
    Balme, G
    TETRAHEDRON LETTERS, 2002, 43 (51) : 9311 - 9314
  • [47] An efficient and diastereoselective synthesis of hydrazino amides via a novel one-pot three-component reaction
    Ramezanpour, Sorour
    Balalaie, Saeed
    Rominger, Frank
    Bijanzadeh, Hamid Reza
    TETRAHEDRON, 2013, 69 (16) : 3480 - 3485
  • [48] One-pot, three-component Synthesis of pyrrolo[2,3-d]pyrimidine Derivatives
    Javahershenas, Ramin
    Khalafy, Jabbar
    JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2018, 62 (01)
  • [49] Highly Efficient One-Pot Three-Component Synthesis of Naphthopyran Derivatives in Water Catalyzed by Phosphates
    Essamlali, Younes
    Amadine, Othmane
    Maati, Houda
    Abdelouahdi, Karima
    Fihri, Aziz
    Zahouily, Mohamed
    Varma, Rajender S.
    Solhy, Abderrahim
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (09): : 1154 - 1159
  • [50] A novel and facile synthesis of N-cyclohexyl-benzofurans by one-pot three-component reaction
    Baghernejad, Bita
    Heravi, Majid M.
    Oskooie, Hossein A.
    Poormohammad, Nargess
    Khorshidi, Maliheh
    Beheshtiha, Yahia Sh
    MOLECULAR DIVERSITY, 2011, 15 (01) : 245 - 248
12345