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Polymer-Supported Pyridine-Bis(oxazoline). Application to Ytterbium Catalyzed Silylcyanation of Benzaldehyde
KTH, Superseded Departments, Chemistry.
KTH, Superseded Departments, Chemistry.
KTH, Superseded Departments, Chemistry.
KTH, Superseded Departments, Chemistry.ORCID iD: 0000-0002-1743-7650
2003 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 20, 3663-3665 p.Article in journal (Refereed) Published
Abstract [en]

Terminal acetylenes containing hydroxy and carboxylic acid groups were subjected to Sonogashira coupling with 4-bromo-2,6-bis[(R)-4-phenyloxazolin-2-yl]pyridine and the resulting pybox derivatives were immobilized on Tentagel resins. Ytterbium(ill) chloride complexes of the polymeric ligands catalyzed the addition of trimethylsilyl cyanide to benzaldehyde with 80-81% ee. The ligands were reused more than 30 times without any loss in selectivity or activity, and the metal complexes could be recovered and reused at least four times, although with slightly decreasing activity.

Place, publisher, year, edition, pages
2003. Vol. 5, no 20, 3663-3665 p.
Keyword [en]
benzaldehyde; oxazoline derivative; polymer; pyridine derivative; ytterbium; addition reaction; article; asymmetric catalysis; chemical reaction; reaction analysis; silylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-6917DOI: 10.1021/ol0353363ISI: 000185565500031OAI: oai:DiVA.org:kth-6917DiVA: diva2:11764
Note
QC 20100809Available from: 2007-03-22 Created: 2007-03-22 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Efficient Synthesis and Analysis of Chiral Cyanohydrins
Open this publication in new window or tab >>Efficient Synthesis and Analysis of Chiral Cyanohydrins
2007 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis deals with the development of new methods for efficient synthesis and analysis in asymmetric catalysis. It focuses on the preparation of chiral cyanohydrins by enantioselective addition of cyanide to prochiral aldehydes.

The initial part of the thesis describes the development of a dual Lewis acid– Lewis base activation system for efficient synthesis of chiral O-acylated and Ocarbonylated cyanohydrins. This system was used for the preparation of a variety of cyanohydrins in high isolated yields and with up to 96% ee. Activation of the cyanide by nucleophilic attack of the Lewis base at the carbonyl carbon atom was supported experimentally.

Secondly, convenient procedures for the synthesis of polymer-bound chiral YbCl3-pybox and Ti-salen complexes are described. The polymeric complexes were employed in cyanation of benzaldehyde.

A T-shaped microreactor was used for screening of reaction conditions for the enantioselective cyanation of benzaldehyde using trimethylsilyl cyanide and acetyl cyanide as cyanide sources. A microreactor charged with the polymeric Tisalen complex was used for enantioselective cyanation of benzaldehyde.

Finally, an enzymatic method for high throughput analysis of ee and conversion of products from chiral Lewis acid–Lewis base-catalysed additions of α- ketonitriles to prochiral aldehydes was developed. The method could be used for the analysis of a variety of O-acylated cyanohydrins. Microreactor technology was successfully combined with high throughput analysis for efficient catalyst optimisation.

Place, publisher, year, edition, pages
Stockholm: KTH, 2007. 54 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2007:11
Keyword
asymmetric catalysis, cyanohydrins, microreactor, polymersupported catalyst, ketonitriles, titanium, lanthanide, Lewis acid, Lewis base
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-4315 (URN)978-91-7178-599-2 (ISBN)
Public defence
2007-04-13, Sal F3, KTH, Lindstedtsvägen 26, Stockholm, 10:15 (English)
Opponent
Supervisors
Note
QC 20100809Available from: 2007-03-22 Created: 2007-03-22 Last updated: 2010-08-09Bibliographically approved

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Moberg, Christina

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