title: One-pot synthesis of enantiopure syn-1,3-diacetates from racemic syn/anti mixtures of 1,3-diols by dynamic kinetic asymmetric transformation.
abstract: A one-pot synthesis of enantiomerically pure syn-1,3-diacetates starting from readily accessible racemic diastereomeric mixtures of 1,3-diols has been realized by combining (i) enzymatic transesterification, (ii) ruthenium-catalyzed epimerization of a secondary alcohol in a diol or diol monoacetate, and (iii) intramolecular acyl migration in a syn-1,3-diol monoacetate. The in situ coupling of these three processes results in an efficient enantioselective synthesis of acyclic syn-1,3-diacetates via combined deracemization-deepimerization and constitutes a dynamic kinetic asymmetric transformation concept. Several differently substituted unsymmetrical, acyclic syn-1,3-diacetates were obtained in yields up to 73% with excellent enantioselectivities (>99%) and good diastereomeric ratios (>90% syn).
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden.
authors.forename: Michaela
authors.initials: M
authors.lastname: Edin
authors.forename: Johannes
authors.initials: J
authors.lastname: Steinreiber
authors.forename: Jan-E
authors.initials: JE
authors.lastname: Bäckvall