Rate-accelerated nonconventional amide synthesis in water: A practical catalytic aldol-surrogate reaction

被引:115
作者
Cho, Seung Hwan
Chang, Sukbok [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
[2] Korea Adv Inst Sci & Technol, Sch Mol Sci BK21, Taejon 305701, South Korea
关键词
beta-hydroxy amides; alkynes; azides; copper; water;
D O I
10.1002/anie.200604358
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) An aldol alternative: Cu-catalyzed hydrative amide synthesis is significantly accelerated in aqueous cosolvent systems. Under environmentally friendly conditions and with N2 released as the single side product, a wide range of propargyl alcohols and sulfonyl azides react to provide β-hydroxy N-sulfonamides in good to excellent yields. Polyhydroxy amides could be synthesized stereoselectively, proving this as a new practical aldol-surrogate strategy. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1897 / 1900
页数:4
相关论文
共 41 条
  • [1] Boron-mediated aldol reaction of carboxylic esters
    Abiko, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (06) : 387 - 395
  • [2] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine
    Bae, I
    Han, H
    Chang, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) : 2038 - 2039
  • [3] Directed methallylations as a synthetic route to 1,3-polyols
    Brzezinski, LJ
    Leahy, JW
    [J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2039 - 2042
  • [4] Carreira E. M., 2000, CATALYTIC ASYMMETRIC
  • [5] Cassidy M.P., 2006, ANGEW CHEM, V118, P3226
  • [6] Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides
    Cassidy, Michael P.
    Raushel, Jessica
    Fokin, Valery V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3154 - 3157
  • [7] Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions
    Chang, Sukbok
    Lee, Minjae
    Jung, Doo Young
    Yoo, Eun Jeong
    Cho, Seung Hwan
    Han, Sun Kyu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) : 12366 - 12367
  • [8] Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
    Cho, SH
    Yoo, EJ
    Bae, L
    Chang, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16046 - 16047
  • [9] Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction
    Cui, Sun-Liang
    Lin, Xu-Feng
    Wang, Yan-Guang
    [J]. ORGANIC LETTERS, 2006, 8 (20) : 4517 - 4520
  • [10] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction
    Davies, HML
    Beckwith, REJ
    Antoulinakis, EG
    Jin, QH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) : 6126 - 6132