Abstract
Biotransformation of ten α-haloacetophenones in the growing culture of the strain Rhodotorula rubra KCh 82 has been carried out. Nine of the substrates underwent an effective enantioselective reduction to the respective (R)-alcohols according to Prelog’s rule, with the exception of 2-chloro-1,2-diphenylethan-1-one that was not transformed by this strain. The expected reduction proceeded without dehalogenation, leading to the respective (R)-halohydrins in high yields. The use of this biocatalyst yielded (R)-2-bromo-1-phenyl-ethan-1-ol (enantiomeric excess (ee) = 97%) and its derivatives: 4'-Bromo- (ee = 99%); 4'-Chloro- (ee > 99%); 4'-Methoxy- (ee = 96%); 3'-Methoxy- (ee = 93%); 2'-Methoxy- (ee = 98%). There were also obtained and characterized 2,4'-dichloro-, 2,2',4'-trichloro- and 2-chloro-4'-fluoro-phenyetan-1-ol with >99% of enantiomeric excesses.
Highlights
Active chlorohydrins are versatile intermediate products in synthesis of biologically active compounds of high importance in the pharmaceutical industry and in agriculture [1]
The strains of the species R. rubra have already been employed for the enantioselective reduction of α-bromoacetophenone (1a) [34]
The authors of this paper described enantioselective reduction of five other α-halogen derivatives of acetophenone
Summary
Active chlorohydrins are versatile intermediate products in synthesis of biologically active compounds of high importance in the pharmaceutical industry and in agriculture [1]. 2014, 15 pharmaceuticals of this kind include denopamine, isoproterenol, formoterol and salmeterol, which are β-adrenergic receptor agonists (all of them with R configuration at the carbon with an OH group). Sci. 2014, 15 pharmaceuticals of this kind include denopamine, isoproterenol, formoterol and salmeterol, which are β-adrenergic receptor agonists (all of them with R configuration at the carbon with an OH group) Both formoterol and salmeterol are used in treatment of chronic obstructive pulmonary disease, being highly selective β2-adrenergic receptor agonists. They are administered via inhalation [2,3,4]. Denopamine is a selective β1-adrenergic agonist and a useful drug for congestive heart failure [5,6]. It is used mainly to prevent cardiac arrhythmia that occurs when the electrical impulses to the heart are not working properly [7,8]
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