Enantioenriched cyanohydrins: Versatile insecticide intermediates
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
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.
IdentifiersURN: urn:nbn:se:kth:diva-71049ISI: 000270256300380OAI: oai:DiVA.org:kth-71049DiVA: diva2:486470
236th ACS National Meeting, Philadelphia, PA
QC 201203062012-01-302012-01-302012-03-06Bibliographically approved