Praktiken im Raum

Abstract

Catalyzed by Rhodococcus erythropolis AJ270 whole cells in an aqueous phosphate buffer - n-hexane biphasic system, racemic axially chiral 2,3-allenenitriles underwent hydrolysis to afford enantioenriched (aR)-2,3-allenamides and (aS)- 2,3-allenoic acids with ees up to >99.5%. Overall biotransformations proceeded through the nitrile hydratase-catalyzed efficient but non-selective hydration of nitriles followed by the amide hydrolysis catalyzed by the substrate-dependent enantioselective amidase. The application of the method has been demonstrated by the transformations of the resulting allene products into highly functionalized heterocyclic compounds with axial chirality of reactants being entirely transferred into or expressed as point chirality of products.