Opposite Enantiomers from Minor Enantiomer Recycling and Dynamic Kinetic Resolution Using a Single Biocatalyst
2011 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20-21, 3980-3984 p.Article in journal (Refereed) Published
A one-pot recycling procedure comprising Lewis acid catalyzed enantioselective addition of acetyl cyanide to (E)-2-butenal to give the O-acetylated cyanohydrin and enzyme-catalyzed conversion of the minor product enantiomer back to (E)-2-butenal provided essentially enantiopure (2R,3E)-2-acetoxy-3-pentenenitrile in close to quantitative yield. The opposite enantiomer was obtained, albeit in lower yield and with lower enantiomeric purity than that observed from the minor enantiomer recycling, by dynamic kinetic resolution consisting of reversible addition of HCN to the aldehyde coupled to enzyme-catalyzed acetylation of the cyanohydrin.
Place, publisher, year, edition, pages
2011. no 20-21, 3980-3984 p.
Aldehydes, Cyanoacetylation, Enzyme catalysis, Lewis acids, Titanium
IdentifiersURN: urn:nbn:se:kth:diva-40679DOI: 10.1002/ejoc.201100467ISI: 000293440900047ScopusID: 2-s2.0-79960329627OAI: oai:DiVA.org:kth-40679DiVA: diva2:443083
FunderSwedish Research CouncilKnut and Alice Wallenberg Foundation
QC 201109232011-09-232011-09-202014-12-02Bibliographically approved