Kinetic resolution of (RS)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol: a metoprolol intermediate and its validation through homology model of Pseudomonas fluorescens lipase

Abstract

Kinetic resolution of (±)-1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol: a metoprolol intermediate and its validation through homology model of Pseudomonas fluorescens lipase.

Production of (S)‐β‐Nitro Alcohols by Enantioselective C−C Bond Cleavage with an R‐Selective Hydroxynitrile Lyase

“…Use of DIPE (81 %), toluene (96.3 %) and n ‐butyl acetate (76.2 %) resulted in moderate to high percentage ee values in the product. Earlier reports have described the use of toluene in biocatalysis to prepare enantiopure β‐nitro alcohols, and lipases were reported to show high activity when toluene was used as a solvent in the kinetic resolution of β‐nitro alcohols and ( S )‐1‐chloro‐3‐[4‐(2‐methoxyethyl)phenoxy]propan‐2‐ol …”

Development of a novel chemoenzymatic route to enantiomerically enriched β-adrenolytic agents. A case study toward propranolol, alprenolol, pindolol, carazolol, moprolol, and metoprolol

“…It is worth mentioning that among the most successful biocatalytic attempts are the lipase-catalyzed kinetic resolutions (KRs) of the respective racemates. In the last two decades, numerous highly efficient lipase-supported methods towards common non-racemic β-blockers, such as acebutolol, 7 alprenolol, 8 atenolol, 9 bufuralol, 10 bunitrolol, 11 carteolol, 12 carvedilol, 13 cloranolol, 14 esmolol, 15 labetalol, 16 metoprolol, 17 moprolol, 18 nifenalol, 19 pindolol, 20 practolol, 21 propranolol, 22 and satolol 22 b were elaborated. Despite these creative efforts invested in the biocatalytic syntheses of non-racemic β-blockers, the reported methods lack generality since any selected API of this class requires an independent and strictly dedicated synthetic strategy.…”