Asymmetric Direct Aldol Reaction of Cyclohexanone Catalyzed by (N′-Benzyl-N′-D-prolyl)-trans-4-hydroxy-L-proline Hydrazide

被引：2
作者：
Cheng Chuanling [1 ]
Wang Wenliang [1 ]
机构：
[1] Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450002, Henan, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 01期
关键词：
asymmetric aldol reaction; proline hydrazide; enantioselectivity; diastereoselectivity; cyclohexanone; VERSATILE CATALYSTS; PROLINE DERIVATIVES; AROMATIC-ALDEHYDES; ORGANIC-MOLECULES; ORGANOCATALYSTS; EFFICIENT; WATER; DESIGN; KETONES; ACID;
D O I：
10.1002/cjoc.201190051
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new proline catalyst, namely (N'-benzyl-N'-D-prolyl)-trans-4-hydroxy-L-proline hydrazide, has been prepared and proved to be a superior catalyst for the asymmetric aldol reaction of cyclohexanone and aromatic aldehydes, affording up to 98 : 2 dr and 98% ee.
引用
收藏
页码：196 / 198
页数：3
相关论文
共 42 条
  • [1] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions
    Berkessel, A
    Koch, B
    Lex, J
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1141 - 1146
  • [2] Rational combination of two privileged chiral backbones: Highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones
    Chen, Jia-Rong
    An, Xiao-Lei
    Zhu, Xiao-Yu
    Wang, Xu-Fan
    Xiao, Wen-Jing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) : 6006 - 6009
  • [3] Sterically and electronically tunable and bifunctional organocatalysts: Design and application in asymmetric aldol reaction of cyclic ketones with aldehydes
    Chen, Jia-Rong
    Li, Xin-Yong
    Xing, Xiao-Ning
    Xiao, Wen-Jing
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) : 8198 - 8202
  • [4] Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions
    Chen, JR
    Lu, HH
    Li, XY
    Cheng, L
    Wan, J
    Xiao, WJ
    [J]. ORGANIC LETTERS, 2005, 7 (20) : 4543 - 4545
  • [5] trans-4-hydroxy-L-proline hydrazide-trifluoroacetic acid as highly stereoselective organocatalyst for the asymmetric direct aldol reaction of cyclohexanone
    Cheng, Chuanling
    Wei, Siyu
    Sun, Jian
    [J]. SYNLETT, 2006, (15) : 2419 - 2422
  • [6] Protonated N′-benzyl-N′-prolyl proline hydrazide as highly enantioselective catalyst for direct asymmetric aldol reaction
    Cheng, CL
    Sun, J
    Wang, C
    Zhang, Y
    Wei, SY
    Jiang, F
    Wu, YD
    [J]. CHEMICAL COMMUNICATIONS, 2006, (02) : 215 - 217
  • [7] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions
    Cobb, AJA
    Shaw, DM
    Longbottom, DA
    Gold, JB
    Ley, SV
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) : 84 - 96
  • [8] Oxazoline-substituted prolinamide-based organocatalysts for the direct intermolecular aldol reaction between cyclohexanone and aromatic aldehydes
    Doherty, Simon
    Knight, Julian G.
    McRae, Amy
    Harrington, Ross W.
    Clegg, William
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (10) : 1759 - 1766
  • [9] Synthesis of Chiral Organocatalysts derived from Aziridines: Application in Asymmetric Aldol Reaction
    Gandhi, Shikha
    Singh, Vinod K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) : 9411 - 9416
  • [10] Direct organocatalytic asymmetric α-chlorination of aldehydes
    Halland, N
    Braunton, A
    Bachmann, S
    Marigo, M
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) : 4790 - 4791
12345