Blockers of beta-adrenergic receptors--a group of chiral agents stereoselective synthesis of beta-blockers
Cizmáriková, R.; Valentová, J.; Hutt, A.J.; Sedláková, S.
Ceska a Slovenska Farmacie Casopis Ceske Farmaceuticke Spolecnosti a Slovenske Farmaceuticke Spolecnosti 54(5): 201-206
2005
ISSN/ISBN: 1210-7816 PMID: 16209433 Document Number: 593718
Besides chromatographic methods and biocatalyzed reactions, another alternative method of obtaining enantiomeric forms of beta-blockers is stereoselective synthesis. This paper links up with two preceding surveys concerning beta-blockers--groups of chiral agents and presents a survey of the hitherto published enantioselective syntheses of (R)- and (S)-enantiomers of beta-blockers. In the group of arylaminoethanols, mainly selective reduction of prochiral ketones in the presence of metallic complexes is used in this type of synthesis. Enantiomerically pure beta-blockers of the aryloxyaminopropanol type are synthesized by means of a reaction of pertinent phenols with different chiral precursors, such as (R) and (S)-chloromethyloxirans, (S)-glycidoltosylate, (S)- or (R)-2,3-O-isopropylideneglyceroltosylate, E-(2S,3S)-3-trimethylsilylglycidol and (S)-3-terc-butyl-5-phenyl-oxazolidine-5-ylmethanol. Many of these chiral semiproducts can be prepared from natural substances, such as D-mannitol and L-ascorbic acid.