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Enantioenriched cyanohydrins: Versatile insecticide intermediates
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2008 (English)In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 236, 95-AGRO- p.Article in journal (Other academic) Published
Abstract [en]

Several pyrethroid insecticides contain cyanoester functions.  Many of these are today used in racemic form or, in case they contain more than a single stereocenter, even as a mixt. of several stereoisomers, although it is known that both aquatic toxicity and biodegrdn. may differ for the two enantiomers.  We have obtained enantioenriched O-acylated cyanohydrins by the addn. of ketonitriles to prochiral aldehydes catalyzed by a chiral Lewis acid and an achiral Lewis base.  By this procedure, (S)-O-acetyl 2-hydroxy-3-butenenitrile was prepd. from acrolein and acetyl cyanide in 67% yield and 73% ee.  This product can be used as an intermediate in the synthesis of glufosinate, (S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid.

Place, publisher, year, edition, pages
2008. Vol. 236, 95-AGRO- p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-71049ISI: 000270256300380OAI: oai:DiVA.org:kth-71049DiVA: diva2:486470
Conference
236th ACS National Meeting, Philadelphia, PA
Note

QC 20120306

Available from: 2012-01-30 Created: 2012-01-30 Last updated: 2017-12-08Bibliographically approved

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Moberg, Christina

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