Direct amino acid catalyzed asymmetric synthesis of polyketide sugars

被引：201

作者：

Casas, J

Engqvist, M

Ibrahem, I

Kaynak, B

Córdova, A

机构：

[1] Stockholm Univ, 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 / 09期

关键词：

aldehydes; aldol reaction; asymmetric catalysis; carbohydrates; hexoses;

D O I：

10.1002/anie.200461400

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Back to the future: In a biomimetic asymmetric synthesis of sugars (see scheme) sequential cross-aldol reactions of simple aldehydes were catalyzed by amino acids. Deoxysugars were obtained with excellent chemoselectivity and up to > 99% ee. This transformation may implicate a prebiotic catalytic pathway in which amino acids transferred their stereochemical information to carbohydrates. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1343 / 1345

页数：3

共 68 条

[1] Precursor-directed biosynthesis of epothilone in Escherichia coli
Boddy, CN
Hotta, K
Tse, ML
Watts, RE
Khosla, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) : 7436 - 7437
[2] Direct catalytic asymmetric aldol reactions of aldehydes
Bogevig, A
Kumaragurubaran, N
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
[3] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones
Bogevig, A
Sundén, H
Córdova, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) : 1109 - 1112
[4] BOGEVIG A, 2004, ANGEW CHEM, V116, P1129
[5] Direct organocatalytic asymmetric α-hydroxymethylation of ketones and aldehydes
Casas, J
Sundén, H
Córdova, A
[J]. TETRAHEDRON LETTERS, 2004, 45 (32) : 6117 - 6119
[6] 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
[7] The direct amino acid-catalyzed asymmetric incorporation of molecular oxygen to organic compounds
Córdova, A
Sundén, H
Engqvist, M
Ibrahem, I
Casas, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) : 8914 - 8915
[8] The direct catalytic asymmetric α-aminooxylation reaction:: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations
Córdova, A
Sundén, H
Bogevig, A
Johansson, M
Himo, F
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) : 3673 - 3684
[9] Direct catalytic asymmetric cross-aldol reactions in ionic liquid media
Córdova, A
[J]. TETRAHEDRON LETTERS, 2004, 45 (20) : 3949 - 3952
[10] The direct catalytic asymmetric cross-Mannich reaction:: A highly enantioselective route to 3-amino alcohols and α-amino acid derivatives
Córdova, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (08) : 1987 - 1997

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