Minor enantiomer recycling: Metal catalyst, organocatalyst and biocatalyst working in concert
2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 44, 12107-12113 p.Article in journal (Refereed) Published
A minor enantiomer recycling one-pot procedure employing two reinforcing chiral catalysts has been developed. Continuous regeneration of the achiral starting material is effected via selective enzyme-catalyzed hydrolysis of the minor product enantiomer from Lewis acid-Lewis base catalyzed addition of acyl cyanides to prochiral aldehydes in a two-phase solvent system. The process provides O-acylated cyanohydrins in close to perfect enantioselectivities, higher than those obtained in the direct process, and in high yields. A combination of a (SS)salen Ti Lewis acid and Candida antarctica lipase B provides the products with R absolute configuration, whereas the opposite enantiomer is obtained from the (R,R)-salen Ti complex and Candida rugosa lipase.
Place, publisher, year, edition, pages
2009. Vol. 15, no 44, 12107-12113 p.
asymmetric catalysis, enantioselectivity, enzyme catalysis, Lewis acids, organocatalysis
IdentifiersURN: urn:nbn:se:kth:diva-10365DOI: 10.1002/chem.200901338ISI: 000272109100036ScopusID: 2-s2.0-72949121762OAI: oai:DiVA.org:kth-10365DiVA: diva2:216255
QC 20100922. Uppdaterad från Manuskript till Artikel (20100922). Tidigare titel "Minor Enantiomer Recycling: Metal Catalyst and Biocatalyst Working in Concert".2009-05-072009-05-072014-12-02Bibliographically approved