Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases

Organic–inorganic nanocrystal reductase to promote green asymmetric synthesis

“…9,12,13 The GcAPRD nanocrystal produced benecial chiral alcohols with excellent enantioselectivities (ee up to >99% (S)) such as (S)-5b (intermediate of EGFR and HER2 kinase inhibitors, a potential cancer treatment agent), 45 (S)-6b (intermediate of sertraline, an obsessive-compulsive disorder medication), 46 and (S)-7b (intermediate of aminotetralin, which can be used to stimulate dopamine, serotonin, and melatonin receptors). 47,48 We were also able to isolate (S)-6b with 84% isolated yield, in a preparative scale reaction catalyzed by the GcAPRD nanocrystal. To the best of our knowledge, this is the rst study to report an ADH nanocrystal with broad substrate specicity.…”

Recent Advances in Enzyme Immobilization Utilizing Nanotechnology for Biocatalysis

“…It enantioselectively reduced aliphatic ketones, including the “difficult to resolve” ethyl propyl ketone, which has only a one-carbon difference between the side chains adjacent to the carbonyl carbon, to achieve 74% yield with 99% S enantiomeric excess ( ee ). Additionally, the Gc APRD nanocrystal produced beneficial chiral alcohols such as ( S )-1-(3-fluorophenyl)­ethanol, an intermediate for EGFR and HER2 kinase inhibitors, which are potential cancer treatment agents, in >99% yield with >99% S ee ; ( S )-1-(3′,4′-dichlorophenyl)­ethanol, an intermediate of sertraline, an obsessive–compulsive disorder medication, in >84% isolated yield with >99% S ee ; and ( S )-1,2,3,4-tetrahydronaphthalen-2-ol, an intermediate for aminotetralin, which can be used to stimulate dopamine, serotonin, and melatonin receptors, , in 91% yield with 96% S ee (Figure ). The Gc APRD nanocrystal was also able to be recycled to reduce 1-phenylethanone up to seven times in a noticeable high yield (>99%) with excellent enantioselectivity (>99% S ee ), which suggested its potential applications in green asymmetric synthesis.…”

Enantioselective Dynamic Process Reduction of α- and β-Tetralone and Stereoinversion of Resulting Alcohols in a Selected Strain Culture

“…The substituted ( S )-β-tetralol is a precursor of a drug used in cardiac arrhythmia [ 15 , 18 , 26 ]. Analogs of 2-aminotetralin have been used in the synthesis of drugs for the treatment of many central nervous system-related disorders [ 3 ] and in the synthesis of antifungal agents [ 25 ].…”