Direct catalytic enantioselective aza-Diels-Alder reactions

被引：218

作者：

Sundén, H

Ibrahem, I

Eriksson, L

Córdova, A

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

[2] Stockholm Univ, Arrhenius Lab, Dept Struct Chem, S-10691 Stockholm, Sweden

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 31期

关键词：

asymmetric catalysis; bicyclic amino acids; cycloaddition; enantioselectivity; ketones;

D O I：

10.1002/anie.200500811

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Proline and its derivatives catalyze the asymmetric one-pot three-component aza-Diels-Alder reaction between unmodified α,β-unsaturated cyclic ketones, aqueous formaldehyde, and aryl amines with excellent chemo- and enantioselectivities (see scheme). Furthermore, this reaction provides a highly enantioselective entry to bicyclic non-proteogenic amino acid derivatives. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4877 / 4880

页数：4

共 74 条

[51] The direct catalytic asymmetric three-component Mannich reaction
List, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) : 9336 - 9337
[52] LOCK R, 1994, LIEBIGS ANN CHEM, P511
[53] Chiral copper complexes of phosphino sulfenyl ferrocenes as efficient catalysts for enantioselective formal Aza Diels-Alder reactions of N-sulfonyl Imines
Mancheño, OG
Arrayás, RG
Carretero, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) : 456 - 457
[54] The first general enantioselective catalytic Diels-Alder reaction with simple α,β-unsaturated ketones
Northrup, AB
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2458 - 2460
[55] Ramachary D. B., 2003, ANGEW CHEM, V115, P4365, DOI [DOI 10.1002/ANGE.200351916, 10.1002/ange.200351916]
[56] Organocatalytic asymmetric domino Knoevenagel/Diels-Alder reactions: A bioorganic approach to the diastereospecific and enantioselective construction of highly substituted spiro[5,5]undecane-1,5,9-triones
Ramachary, DB
Chowdari, NS
Barbas, CF
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) : 4233 - 4237
[57] Novel organic catalysts for the direct enantioselective α-oxidation of carbonyl compounds
Sundén, H
Dahlin, N
Ibrahem, I
Adolfsson, H
Córdova, A
[J]. TETRAHEDRON LETTERS, 2005, 46 (19) : 3385 - 3389
[58] Direct amino acid catalyzed asymmetric α oxidation of ketones with molecular oxygen
Sundén, H
Engqvist, M
Casas, J
Ibrahem, I
Córdova, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) : 6532 - 6535
[59] SUNDEN H, 2004, ANGEW CHEM, V16, P6694
[60] Tietze LF, 1997, TOP CURR CHEM, V189, P1

← 1 2 3 4 5 6 7 8 →