Enantioselective desymmetrization of prochiral cyclohexanone derivatives via the organocatalytic direct Aldol reaction

被引：57
作者：
Jiang, Jun
He, Long
Luo, Shi-Wei
Cun, Lin-Feng
Gong, Liu-Zhu [1 ]
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
[3] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[4] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2007年 / 07期
关键词：
D O I：
10.1039/b615043h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Asymmetric desymmetrization of 4-substituted cyclohexanones using proline amide-catalyzed direct aldol reaction afforded beta-hydroxyketones with three stereogenic centers in high enantioselectivities of up to > 99% ee.
引用
收藏
页码：736 / 738
页数：3
相关论文
共 56 条
[1]   The direct catalytic asymmetric cross-aldol reaction of aldehydes [J].
Alcaide, B ;
Almendros, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (08) :858-860
[2]   An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3•7H2O-NaI system.: Novel methodology for the synthesis of (S)-(-)-pulegone [J].
Bartoli, G ;
Bosco, M ;
Dalpozzo, R ;
Giuliani, A ;
Marcantoni, E ;
Mecozzi, T ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :9111-9114
[3]   Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions [J].
Berkessel, A ;
Koch, B ;
Lex, J .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1141-1146
[4]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[5]   Direct catalytic asymmetric aldol reactions of aldehydes [J].
Bogevig, A ;
Kumaragurubaran, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2002, (06) :620-621
[6]   Lithium N-trityl-N-(R)-1-phenethylamide, a readily available and useful base for the enantioselective formation of chiral enolates from achiral ketones [J].
Busch-Petersen, J ;
Corey, EJ .
TETRAHEDRON LETTERS, 2000, 41 (36) :6941-6944
[7]   Direct amino acid catalyzed asymmetric synthesis of polyketide sugars [J].
Casas, J ;
Engqvist, M ;
Ibrahem, I ;
Kaynak, B ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1343-1345
[8]   Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions [J].
Chen, JR ;
Lu, HH ;
Li, XY ;
Cheng, L ;
Wan, J ;
Xiao, WJ .
ORGANIC LETTERS, 2005, 7 (20) :4543-4545
[9]   Asymmetric alcoholysis of cyclic anhydrides [J].
Chen, YG ;
McDaid, P ;
Deng, L .
CHEMICAL REVIEWS, 2003, 103 (08) :2965-2983
[10]   Protonated N′-benzyl-N′-prolyl proline hydrazide as highly enantioselective catalyst for direct asymmetric aldol reaction [J].
Cheng, CL ;
Sun, J ;
Wang, C ;
Zhang, Y ;
Wei, SY ;
Jiang, F ;
Wu, YD .
CHEMICAL COMMUNICATIONS, 2006, (02) :215-217
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