155486-16-1Relevant articles and documents
Biocatalytic cascade for the synthesis of enantiopure β-azidoalcohols and β-hydroxynitriles
Schrittwieser, Joerg H.,Lavandera, Ivan,Seisser, Birgit,Mautner, Barbara,Kroutil, Wolfgang
experimental part, p. 2293 - 2298 (2009/08/17)
A three-step, two-enzyme, one-pot reaction sequence starting from prochiral a-chloroketones leading to enantiopure (3- azidoalcohols and (3-hydroxynitriles is described. Asymmetric bioreduction of a-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide and nucleophilic ring opening with azide, N3-, or cyanide, CN-, both catalysed by a nonselective halohydrin dehalogenase (Hhe) proceeded with full retention of configuration to give enantiopure (-azidoalcohols and (3-hydroxynitriles, respectively. Both enantiomers of various optically pure (-azidoalcohols and (-hydroxynitriles were synthesised.