Lipase kinetic enantiomeric resolution of 1-heteroarylethanols. Issue 7 (1st May 2016)

• Record Type: Journal Article
• Authors: Kucher, Olexandr V.; Kolodyazhnaya, Anastasiya O.; Smolii, Oleg B.; Nazarenko, Nadiya K.; Kubyshkin, Vladimir; Mykhailiuk, Pavel K.; Tolmachev, Andrey A.
• Is Part Of: Tetrahedron, asymmetry. Volume 27:Issue 7/8(2016)
• Page Start: 341
• Page End: 345
• Publication Date: 2016-05-01
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2016.02.012
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: The use of lipases offers a simple and straightforward method toward various chiral secondary alcohols. Here we examined the lipase resolution of 1-heteroarylethanols. Racemic substrates were subjected to a two step resolution strategy. The difference between the substituent sizes around the chiral fragment allowed the successful isolation of the ( S )-alcohols with assistance of the Burkholderia cepacia lipase (ee ⩾ 96%). The ( R )-isomers were obtained after hydrolysis of the enantioenriched O -acetylated alcohols either with Candida antarctica lipase B or with potassium carbonate. The performance of the latter step was found to be substrate dependent. Abstract : (1 S )-1-(2-Methyl-1, 3-thiazol-4-yl)ethanol: C6 H9 NOS ee = 98% [ α ]D 20 = −52.3 ( c 1.4, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S ) Abstract : (1 S )-1-(1, 3-Thiazol-5-yl)ethanol: C5 H7 NOS ee = 99% [ α ]D 20 = −13.1 ( c 1.3, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S ) Abstract : (1 S )-1-(5-Methyl-1, 3, 4-oxadiazol-2-yl)ethanol: C5 H8 N2 O2 ee = 96% [ α ]D 20 = −17.9 ( c 1.0, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S ) Abstract : (1 S )-1-(1-Methyl-1 H -pyrazol-4-yl)ethanol: C6 H10 N2 O ee = 98% [ α ]D 20 = −7.7 ( c 1.3, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S ) Abstract : (1 S )-1-(1-Phenyl-1 H -pyrazol-4-yl)ethanol: C11 H12 N2 O ee = 96% [ α ]D 20 = −14.6 ( c 1.1, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S ) Abstract : (1 S )-1-(1-Benzyl-1 H -pyrazol-4-yl)ethanol: C12 H14 N2 O ee = 97% [ α ]D 20 = −4.2 ( c 1.6, EtOH) Source of chirality: Burkholderia cepacia lipase resolution Absolute configuration: (1 S )