Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds

被引:294
|
作者
Duthaler, RO [1 ]
机构
[1] Novartis Inst Biomed Res, CH-4002 Basel, Switzerland
关键词
amination; azodicarboxylates; catalysis; enantioselectivity; proline;
D O I
10.1002/anie.200390283
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple, direct, and highly enantioselective α-amination of carbonyl compounds 1 with azodicarboxylates 2 no longer requires prior enolization of the substrate. The magic small-organic-molecule catalyst for this reaction in dichloromethane at room temperature is once again L-proline (3).
引用
收藏
页码:975 / 978
页数:4
相关论文
共 18 条
  • [1] The proline-catalyzed asymmetric Amination of branched aldehydes
    Baumann, Thomas
    Vogt, Henning
    Braese, Stefan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) : 266 - 282
  • [2] Direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones
    Hayashi, Y
    Yamaguchi, J
    Sumiya, T
    Hibino, K
    Shoji, M
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18): : 5966 - 5973
  • [3] Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes
    List, B
    Pojarliev, P
    Castello, C
    ORGANIC LETTERS, 2001, 3 (04) : 573 - 575
  • [4] Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline
    Ait-Youcef, Ramzi
    Kalch, Delphine
    Moreau, Xavier
    Thomassigny, Christine
    Greck, Christine
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (05) : 377 - 380
  • [5] Diastereoselective synthesis of furanose and pyranose substituted glycine and alanine derivatives via proline-catalyzed asymmetric α-amination of aldehydes
    Petakamsetty, Ramu
    Ansari, Anas
    Ramapanicker, Ramesh
    CARBOHYDRATE RESEARCH, 2016, 435 : 37 - 49
  • [6] Formation of optically active functionalized β-hydroxy nitrones using a proline catalyzed aldol reaction of aldehydes with carbonyl compounds and hydroxylamines
    Bogevig, A
    Poulsen, TB
    Zhuang, W
    Jorgensen, KA
    SYNLETT, 2003, (12) : 1915 - 1918
  • [7] An Efficient Ionic Liquid Additive for Proline-catalyzed Direct Asymmetric Aldol Reactions between Cyclic Ketones and Aromatic Aldehydes
    Qian, Yunbo
    Zheng, Xin
    Wang, Xu
    Xiao, Shiyong
    Wang, Yongmei
    CHEMISTRY LETTERS, 2009, 38 (06) : 576 - 577
  • [8] Direct organo-catalytic asymmetric α-amination of aldehydes - A simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids
    Bøgevig, Anders
    Juhl, Karsten
    Kumaragurubaran, Nagaswamy
    Zhuang, Wei
    Jørgensen, Karl Anker
    1790, Wiley-VCH Verlag (41)
  • [9] Direct organo-catalytic asymmetric α-amination of aldehydes -: A simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids
    Bogevig, A
    Juhl, K
    Kumaragurubaran, N
    Zhuang, W
    Jorgensen, KA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (10) : 1790 - +
  • [10] Organocatalytic Asymmetric Decarboxylative Amination of β-Keto Acids: Access to Optically Active α-Amino Ketones and 1,2-Amino Alcohols
    Wei, Yi
    Zhang, Heng-Xia
    Zeng, Jun-Liang
    Nie, Jing
    Ma, Jun-An
    ORGANIC LETTERS, 2017, 19 (08) : 2162 - 2165