A new approach for an organocatalytic multicomponent domino asymmetric reaction

被引：227

作者：

Carlone, Armando ^{[1
]}

Cabrera, Silvia ^{[1
]}

Marigo, Mauro ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Catalysis, Danish Natl Res Fdn, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 07期

关键词：

aldehydes; asymmetry; domino reactions; multicomponent reactions; organocatalysis;

D O I：

10.1002/anie.200604479

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

As easy as pouring! Three C-C bonds, up to three stereocenters, and ee values greater than 97% are created in a new organocatalyzed multicomponent domino reaction (see picture; TMS = trimethylsilyl; EWG = electron-withdrawing group). Very high enantioselectivity, control of the substituents, easy handling, and user-friendly reaction conditions are key features of this transformation. (Figure Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1101 / 1104

页数：4

共 60 条

[1] [Anonymous], 2003, ANGEW CHEM
[2] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
Bertelsen, Slren
Marigo, Mauro
Brandes, Sebastian
Diner, Peter
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
[4] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions
Brandau, Sven
Maerten, Eddy
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14986 - 14991
[5] A simple asymmetric organocatalytic approach to optically active cyclohexenones
Carlone, Armando
Marigo, Mauro
North, Chris
Landa, Aitor
Jorgensen, Karl Anker
[J]. CHEMICAL COMMUNICATIONS, 2006, (47) : 4928 - 4930
[6] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds
Cativiela, C
Díaz-de-Villegas, MD
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 645 - 732
[7] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds
Cativiela, C
Diaz-de-Villegas, MD
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (20) : 3517 - 3599
[8] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL (E)-2-CYANOCINNAMATES .2. SYNTHESIS OF THE 4 1-AMINO-2-PHENYL-1-CYCLOHEXANECARBOXYLIC ACIDS IN ENANTIOMERICALLY PURE FORM
CATIVIELA, C
AVENOZA, A
PARIS, M
PEREGRINA, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7774 - 7778
[9] Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids
Chi, Yonggui
Gellman, Samuel H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6804 - 6805
[10] Proline-catalyzed asymmetric assembly reactions:: enzyme-like assembly of carbohydrates and polyketides from three aldehyde substrates
Chowdari, NS
Ramachary, DB
Córdova, A
Barbas, CF
[J]. TETRAHEDRON LETTERS, 2002, 43 (52) : 9591 - 9595

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