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 50 条
  • [21] 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
  • [22] L-Proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric α-aminoxylation of aldehydes and ketones
    Guo, Hai-Ming
    Niu, Hong-Ying
    Xue, Meng-Xia
    Guo, Qi-Xiang
    Cun, Lin-Feng
    Mi, Ai-Qiao
    Jiang, Yao-Zhong
    Wang, Jian-Ji
    GREEN CHEMISTRY, 2006, 8 (08) : 682 - 684
  • [23] L-proline catalyzed asymmetric transfer aldol reaction between diacetone alcohol and aldehydes
    Chandrasekhar, S
    Narsihmulu, C
    Reddy, NR
    Sultana, SS
    CHEMICAL COMMUNICATIONS, 2004, (21) : 2450 - 2451
  • [24] L-Proline amide-catalyzed direct asymmetric aldol reaction of aldehydes with chloroacetone
    He, L
    Tang, Z
    Cun, LF
    Mi, AQ
    Jiang, YZ
    Gong, LZ
    TETRAHEDRON, 2006, 62 (2-3) : 346 - 351
  • [25] An Easy and General Iron-catalyzed Reductive Amination of Aldehydes and Ketones with Anilines
    Fleischer, Steffen
    Zhou, Shaolin
    Junge, Kathrin
    Beller, Matthias
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (09) : 2240 - 2245
  • [26] Organocatalytic asymmetric Michael addition of aldehydes and ketones to nitroalkenes catalyzed by adamantoyl L-prolinamide
    Wang, Yongchao
    Li, Dong
    Lin, Jun
    Wei, Kun
    RSC ADVANCES, 2015, 5 (08) : 5863 - 5874
  • [27] Iridium-catalyzed direct asymmetric reductive amination of aromatic ketones
    Huang, Haizhou
    Wu, Zitong
    Gao, Guorui
    Zhou, Le
    Chang, Mingxin
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (10): : 1976 - 1980
  • [28] Asymmetric Allylation of Aldehydes Catalyzed by Simple Dual Small Organic Molecules: L-Proline and L-Prolinol
    Chen, Guo-hong
    Liu, Ling-yan
    Wei, Xiao-ning
    Chang, Wei-xing
    Li, Jing
    CHEMISTRY LETTERS, 2010, 39 (09) : 1013 - 1015
  • [29] The scope of the direct proline-catalyzed asymmetric addition of ketones to imines
    Notz, W
    Watanabe, S
    Chowdari, NS
    Zhong, GF
    Betancort, JM
    Tanaka, F
    Barbas, CF
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1131 - 1140
  • [30] Proline catalyzed asymmetric aldol reaction between methyl ketones and α-ketoesters
    Wang Ya-Jun
    Shen Zong-Xuan
    Li Bin
    Zhang Ya-Wen
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (09) : 1196 - 1199