Chiral oligomers by iterative tandem catalysis

被引：66

作者：

van As, BAC

van Buijtenen, J

Heise, A

Broxterman, QB

Verzijl, GKM

Palmans, ARA

Meijer, EW

机构：

[1] Eindhoven Univ Technol, Lab Macromol & Organ Chem, NL-5600 MB Eindhoven, Netherlands

[2] DSM Res & Patents, PM CT, LS ASC&D, NL-6160 MD Geleen, Netherlands

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 28期

关键词：

D O I：

10.1021/ja052347d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iterative tandem catalysis is presented as a flexible tool for obtaining chiral macromolecules from racemic or prochiral monomers. Here, we combine lipase-catalyzed ring-opening of ω-substituted lactones with ruthenium-catalyzed racemization. In a two-pot system, enantioenriched oligomers of 6-methyl-ε-caprolactone were synthesized, which could not have been obtained by enzymatic ring-opening alone. A one-pot experiment proved highly promising in developing a novel route toward enantiopure polyesters. Copyright © 2005 American Chemical Society.

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页码：9964 / 9965

页数：2

相关论文

共 17 条

[1] Concepts of nature in organic synthesis: Cascade catalysis and multistep conversions in concert [J].

Bruggink, A ;

Schoevaart, R ;

Kieboom, T .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (05) :622-640

[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[3] Aminocyclopentadienyl ruthenium complexes as racemization catalysts for dynamic kinetic resolution of secondary alcohols at ambient temperature [J].

Choi, JH ;

Choi, YK ;

Kim, YH ;

Park, ES ;

Kim, EJ ;

Kim, MJ ;

Park, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1972-1977

[4] SIMPLE P-31 NMR METHOD FOR THE DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS NOT REQUIRING CHIRAL AUXILIARY COMPOUNDS [J].

FERINGA, BL ;

SMAARDIJK, A ;

WYNBERG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) :4798-4799

[5] SELECTIVE HYDROGENATION OF CYCLIC ESTER TO ALPHA,OMEGA-DIOL CATALYZED BY CATIONIC RUTHENIUM COMPLEXES WITH TRIALKYLPHOSPHINE LIGANDS [J].

HARA, Y ;

INAGAKI, H ;

NISHIMURA, S ;

WADA, K .

CHEMISTRY LETTERS, 1992, (10) :1983-1986

[6] Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially alpha-amino acids [J].

Janes, LE ;

Kazlauskas, RJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3719-3733

[7] Enzymatic resolution of alcohols coupled with ruthenium-catalyzed racemization of the substrate alcohol [J].

Larsson, ALE ;

Persson, BA ;

Backvall, JE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (11) :1211-1212

[8] Highly compatible metal and enzyme catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature [J].

Martín-Matute, B ;

Edin, M ;

Bogár, K ;

Bäckvall, JE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (47) :6535-6539

[9] Chemoenzymatic dynamic kinetic resolution [J].

Pàmies, O ;

Bäckvall, JE .

TRENDS IN BIOTECHNOLOGY, 2004, 22 (03) :130-135

[10] Combination of enzymes and metal catalysts.: A powerful approach in asymmetric catalysis [J].

Pàmies, O ;

Bäckvall, JE .

CHEMICAL REVIEWS, 2003, 103 (08) :3247-3261