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

来源：

SYNLETT | 2007年 / 11期

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

页码：1667 / 1670

页数：4

共 63 条

[1] Organocatalytic asymmetric conjugate additions
Almasi, Diana
Alonso, Diego A.
Najera, Carmen
[J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
[2] [Anonymous], 2004, ANGEW CHEM, V116, P1292
[3] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions
Arai, S
Nakayama, K
Ishida, T
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (22) : 4215 - 4218
[4] Bako P, 1997, SYNLETT, P291
[5] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results
Ballini, R
Bosica, G
Fiorini, D
Palmieri, A
Petrini, M
[J]. 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
Brandau, Sven
Landa, Aitor
Franzen, Johan
Marigo, Mauro
Jorgensen, Karl Anker
[J]. 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
Carlone, Armando
Cabrera, Silvia
Marigo, Mauro
Jorgensen, Karl Anker
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) : 1101 - 1104

← 1 2 3 4 5 6 7 →