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O-Acylated Cyanohydrins: Versatile Intermediates and Products
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry.ORCID iD: 0000-0002-1743-7650
2007 (English)In: Chimica Oggi, ISSN 0392-839X, Vol. 25, no 5, 14-15 p.Article in journal (Refereed) Published
Abstract [en]

Addition of ketonitriles to prochiral aromatic or aliphatic aldehydes in the presence of a catalytic system consisting of a chiral Lewis acid and an achiral Lewis base gives access to chiral enantioenriched O-acylated cyanohydrins. The products are useful for diverse potential applications.

Place, publisher, year, edition, pages
2007. Vol. 25, no 5, 14-15 p.
Keyword [en]
lewis-base activation; asymmetric-synthesis; aldehydes; esters; optimization; insecticides; degradation; complexes; sediment; cyanide
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-10364ISI: 000256192700003Scopus ID: 2-s2.0-36048999872OAI: oai:DiVA.org:kth-10364DiVA: diva2:216253
Note

QC 20100818

Available from: 2009-05-07 Created: 2009-05-07 Last updated: 2016-12-19Bibliographically approved
In thesis
1. New Methods for Chiral Cyanohydrin Synthesis
Open this publication in new window or tab >>New Methods for Chiral Cyanohydrin Synthesis
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with method development in asymmetric catalysis and specifically syntheses of enantioenriched O-functionalized cyanohydrins.

The first part describes the development of a method for the synthesis of O‑alkoxycarbonylated and O-acylated cyanohydrins. Ethyl cyanoformate and acyl cyanides were added to aldehydes in a reaction catalyzed by a chiral dimeric Ti-salen complex together with a tertiary amine. High yields and enantioselectivities were in most cases obtained. Mechanistic studies were performed and a reaction mechanism was proposed. ­

The second part describes a method in which the undesired minor enantiomer in a Lewis acid–Lewis base-catalyzed acylcyanation is continuously recycled into prochiral starting material. Close to enantiopure O‑acylated cyanohydrins were obtained in high yields.

The third part deals with asymmetric acylcyanations of ketones. Acetyl cyanide was found to add to α‑ketoesters in a reaction catalyzed by a chiral Lewis base. Yields up to 77% and 82% ee were obtained.

The final part describes an enzymatic method for high-throughput analysis of O‑acylated cyanohydrins. The enantiomeric excess and conversion were determined for products obtained from a number of aromatic and aliphatic aldehydes.

Place, publisher, year, edition, pages
Stockholm: KTH, 2009. 54 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:12
Keyword
acyl cyanides, asymmetric synthesis, biocatalysis, cyanide, cyanohydrins, dual activation, enzymes, high-throughput screening, Lewis acid, Lewis base, metal catalysis, minor enantiomer recycling, salen, titanium
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-10205 (URN)978-91-7415-263-0 (ISBN)
Public defence
2009-05-08, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100818Available from: 2009-05-07 Created: 2009-04-06 Last updated: 2010-09-22Bibliographically approved

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