Organocatalytic Enantioselective Cross-Aldol Reactions of Aldehydes with Isatins: Formation of Two Contiguous Quaternary Centered 3-Substituted 3-Hydroxyindol-2-ones

被引:79
作者
Xue, Fei [1 ]
Zhang, Shilei [1 ]
Liu, Lu [1 ]
Duan, Wenhu [1 ]
Wang, Wei [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
[2] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA
关键词
aldehydes; aldol; isatins; organocatalysis; CATALYTIC ASYMMETRIC ALDOL; HIGHLY EFFICIENT CATALYST; NATURAL-PRODUCTS; CARBON CENTERS; KETONES; PROLINE; MICHAEL; (R)-CONVOLUTAMYDINE; STEREOCENTERS; CONSTRUCTION;
D O I
10.1002/asia.200900243
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Good neighbors: Cross-aldol reactions of isatins with aldehydes, catalyzed by (S)-pyrrolidine tetrazole are developed. In the process, two contiguous quaternary centers and one chiral carbon are created simultaneously with good efficiency. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1664 / 1667
页数:4
相关论文
共 62 条
  • [1] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions
    Allemann, C
    Gordillo, R
    Clemente, FR
    Cheong, PHY
    Houk, KN
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 558 - 569
  • [2] [Anonymous], 2007, ANGEW CHEM, DOI DOI 10.1103/PHYSREVLETT.112.077206
  • [3] [Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
  • [4] Organocatalytic Formation of Quaternary Stereocenters
    Bella, Marco
    Gasperi, Tecla
    [J]. SYNTHESIS-STUTTGART, 2009, (10): : 1583 - 1614
  • [5] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
  • [6] CARREIR EM, 2000, CATALYTIC ASYMMETRIC
  • [7] L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone
    Chen, Gang
    Wang, Ye
    He, Hongping
    Gao, Suo
    Yang, Xiaosheng
    Hao, Xiaojiang
    [J]. HETEROCYCLES, 2006, 68 (11) : 2327 - 2333
  • [8] Organocatalytic asymmetric aldol reaction of ketones with isatins: straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones
    Chen, Jia-Rong
    Liu, Xiao-Peng
    Zhu, Xiao-Yu
    Li, Liang
    Qiao, Yong-Feng
    Zhang, Jian-Ming
    Xiao, Wen-Jing
    [J]. TETRAHEDRON, 2007, 63 (42) : 10437 - 10444
  • [9] 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
  • [10] Stereoselective construction of quaternary stereocenters
    Christoffers, J
    Baro, A
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) : 1473 - 1482