140924-05-6Relevant articles and documents
Ruthenium- and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols
Persson, B. Anders,Larsson, Anna L. E.,Le Ray, Mika?l,B?ckvall, Jan-E.
, p. 1645 - 1650 (1999)
Enzymatic resolution of secondary alcohols under substrate racemizing conditions was studied using an immobilized lipase from Candida antarctica in the presence of a ruthenium catalyst. A specifically designed acyl donor, 4- chlorophenyl acetate, was found to be compatible with both catalysts and resulted in an efficient dynamic kinetic resolution. Studies of the reaction in different solvents showed that nonpolar solvents gave the best results. With this process, a variety of racemic secondary alcohols were transformed to the corresponding enantiomerically pure acetates, making efficient use of all starting material. In most cases, the reaction proceeded with >99% ee and in good yield.
Chemoenzymatic dynamic kinetic resolution of β-halo alcohols. An efficient route to chiral epoxides
Pamies, Oscar,Baeckvall, Jan-E.
, p. 9006 - 9010 (2007/10/03)
Enzymatic resolution of β-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when β-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.
Enzyme Assisted Preparation of Enantiomerically Pure β-Adrenergic Blockers III. Optically Active Chlorohydrin Derivatives and Their Conversion
Ader, Ulrich,Schneider, Manfred P.
, p. 521 - 524 (2007/10/02)
Optical active chlorohydrin derivatives 2a-m and 3a-m of both enantiomeric series were prepared via both enzymatic hydrolyses and acyltransfer reactions catalysed by a highly selective lipase from Pseudomonas sp..The resulting building blocks were further transformed into the corresponding β-blockers of high enantiomeric purity.
