N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols

被引:271
|
作者
Movassaghi, M [1 ]
Schmidt, MA [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol050773y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A catalytic amidation of unactivated esters with amino alcohols is described. A series of solution studies in addition to the first X-ray structure of a carbene-alcohol complex support a carbene-base nucleophile activation mechanism.
引用
收藏
页码:2453 / 2456
页数:4
相关论文
共 50 条
  • [1] N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters
    Maki, Brooks E.
    Scheidt, Karl A.
    ORGANIC LETTERS, 2008, 10 (19) : 4331 - 4334
  • [2] N-Heterocyclic carbene-catalyzed conversion of α-amino alcohols to their corresponding epoxides
    Goralski, Sean
    Saliba, Bianca
    Overly, Kenneth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [3] N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
    Alanthadka, Anitha
    Maheswari, C. Uma
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1199 - 1203
  • [4] N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds
    Hirano, Keiichi
    Biju, Akkattu T.
    Piel, Isabel
    Glorius, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14190 - +
  • [5] N-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols
    Phillips, Eric M.
    Riedrich, Matthias
    Scheidt, Karl A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13179 - 13181
  • [6] N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
    Gelat, Fabien
    Patra, Atanu
    Pannecoucke, Xavier
    Biju, Akkattu T.
    Poisson, Thomas
    Besset, Tatiana
    ORGANIC LETTERS, 2018, 20 (13) : 3897 - 3901
  • [7] Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
    Singh, Ashmita
    Narula, Anudeep Kumar
    SYNLETT, 2021, 32 (07) : 718 - 722
  • [8] N-Heterocyclic Carbene-Catalyzed α-Alkylation of Ketones with Primary Alcohols
    Zhu, Yanfang
    Cai, Chun
    Lu, Guoping
    HELVETICA CHIMICA ACTA, 2014, 97 (12) : 1666 - 1671
  • [9] N-Heterocyclic carbene-catalyzed oxidations
    Maki, Brooks E.
    Chan, Audrey
    Phillips, Eric M.
    Scheidt, Karl A.
    TETRAHEDRON, 2009, 65 (16) : 3102 - 3109
  • [10] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes
    Biju, Akkattu T.
    Wurz, Nathalie E.
    Glorius, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5970 - +