Asymmetric organocatalytic domino reactions of γ-nitroketones and enals

被引:74
作者
Enders, Dieter [1 ]
Narine, Arun A. [1 ]
Benninghaus, Thomas R. [1 ]
Raabe, Gerhard [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
Michael additions; aldol reactions; asymmetric synthesis; domino reactions; organocatalysis;
D O I
10.1055/s-2007-984517
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral Substituted cyclohexene carbaldehydes are readily synthesized in excellent enantiomeric excesses from simple nitroketone and enal precursors. The domino Michael addition-aldol condensation reaction catalyzed by a chiral secondary amine involves tandem iminium-enamine activation.
引用
收藏
页码:1667 / 1670
页数:4
相关论文
共 63 条
[1]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[2]  
[Anonymous], 2004, ANGEW CHEM, V116, P1292
[3]   Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions [J].
Arai, S ;
Nakayama, K ;
Ishida, T ;
Shioiri, T .
TETRAHEDRON LETTERS, 1999, 40 (22) :4215-4218
[4]  
Bako P, 1997, SYNLETT, P291
[5]   Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A ;
Petrini, M .
CHEMICAL REVIEWS, 2005, 105 (03) :933-971
[6]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7]  
Brandau S., 2006, ANGEW CHEM, V118, P4411
[8]   Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].
Brandau, Sven ;
Landa, Aitor ;
Franzen, Johan ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309
[9]  
CARLONE A, 2007, ANGEW CHEM, V119, P1119
[10]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104