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
[31]   Optimization of the catalytic asymmetric addition of nitroalkanes to cyclic enones with trans-4,5-methano-L-proline [J].
Hanessian, Stephen ;
Shao, Zhihui ;
Warrier, Jayakumar S. .
ORGANIC LETTERS, 2006, 8 (21) :4787-4790
[32]   A new asymmetric organocatalytic nitrocyclopropanation reaction [J].
Hansen, Henriette M. ;
Longbottom, Deborah A. ;
Ley, Steven V. .
CHEMICAL COMMUNICATIONS, 2006, (46) :4838-4840
[33]   Enantioselective organo-cascade catalysis [J].
Huang, Y ;
Walji, AM ;
Larsen, CH ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15051-15053
[34]   Enantioselective Michael reaction of nitroalkanes and chalcones by phase-transfer catalysis using chiral quaternary ammonium salts [J].
Kim, DY ;
Huh, SC .
TETRAHEDRON, 2001, 57 (43) :8933-8938
[35]   Asymmetric organocatalytic conjugate addition of malonates to enones using a proline tetrazole catalyst [J].
Knudsen, KR ;
Mitchell, CET ;
Ley, SV .
CHEMICAL COMMUNICATIONS, 2006, (01) :66-68
[36]   UNEXPECTED CHANGE OF ABSOLUTE-CONFIGURATION IN ASYMMETRIC MICHAEL ADDITION OF METHYL VINYL KETONE TO 2-NITROCYCLOALKANONES [J].
LATVALA, A ;
STANCHEV, S ;
LINDEN, A ;
HESSE, M .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :173-176
[37]  
Lelais G, 2006, ALDRICHIM ACTA, V39, P79
[38]   One-pot approach to chiral chromenes via enantioselective organocatalytic domino oxa-Michael-aldol reaction [J].
Li, Hao ;
Wang, Jian ;
E-Nunu, Timiyin ;
Zu, Liansuo ;
Jiang, Wei ;
Wei, Shaohua ;
Wang, Wei .
CHEMICAL COMMUNICATIONS, 2007, (05) :507-509
[39]   One-pot organocatalytic domino Michael-aldol and intramolecular SN2 reactions.: Asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives [J].
Marigo, M ;
Bertelsen, S ;
Landa, A ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) :5475-5479
[40]   Organocatalytic direct asymmetric α-heteroatom functionalization of aldehydes and ketones [J].
Marigo, M ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2006, (19) :2001-2011