Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline

被引:14
作者
Ait-Youcef, Ramzi [1 ]
Kalch, Delphine [1 ]
Moreau, Xavier [1 ]
Thomassigny, Christine [1 ]
Greck, Christine [1 ]
机构
[1] Univ Versailles St Quentin En Yvelines, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France
关键词
Electrophilic amination; organocatalysis; tert-butoxyproline; azodicarboxylate; alpha-hydrazinoalcohol; ELECTROPHILIC AMINATION; CARBONYL-COMPOUNDS; ORGANOCATALYSIS; ACID; CARBANIONS;
D O I
10.2174/157017809788681293
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric electrophilic alpha-amination of aldehydes and ketones is described using trans-3-tert-butoxy-L-proline and trans-4-tert-butoxy-L-proline as efficient catalysts. Good yields and high enantioselectivities are obtained working at 0 degrees C or at room temperature with a catalyst loading of only 5 mol%.
引用
收藏
页码:377 / 380
页数:4
相关论文
共 26 条
  • [1] Thermal effects in the organocatalytic asymmetric α-amination of disubstituted aldehydes with azodicarboxylates:: A high-temperature organocatalysis
    Baumann, Thomas
    Baechle, Michael
    Hartmann, Caroline
    Braese, Stefan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (13) : 2207 - 2212
  • [2] The proline-catalyzed asymmetric Amination of branched aldehydes
    Baumann, Thomas
    Vogt, Henning
    Braese, Stefan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) : 266 - 282
  • [3] Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
  • [4] 2-Y
  • [5] Dembech P, 2000, CHEM-EUR J, V6, P1281, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1281::AID-CHEM1281>3.0.CO
  • [6] 2-F
  • [7] ELECTROPHILIC AMINATION OF CARBANIONS
    ERDIK, E
    AY, M
    [J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1947 - 1980
  • [8] Genet J.-P., 2000, MODERN AMINATION MET, P65, DOI DOI 10.1002/9783527613182.
  • [9] Synthesis of both enantiomers of trans 3-hydroxypipecolic acid.
    Greck, C
    Ferreira, F
    Genet, JP
    [J]. TETRAHEDRON LETTERS, 1996, 37 (12) : 2031 - 2034
  • [10] Asymmetric electrophilic α-amination of carbonyl groups
    Greck, C
    Drouillat, B
    Thomassigny, C
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) : 1377 - 1385