1397495-70-3Relevant academic research and scientific papers
Enhanced biocatalytic performance of bacterial laccase from Streptomyces sviceus: Application in the Michael addition sequence towards 3-arylated 4-oxochromanes
Suljic, Sanel,Mortzfeld, Frederik B.,Gunne, Matthias,Urlacher, Vlada B.,Pietruszka, J?rg
, p. 1380 - 1385 (2015)
A fast and efficient laccase-catalysed oxidation/Michael addition sequence is performed using the bacterial laccase Ssl 1 from Streptomyces sviceus under basic conditions to provide a new class of 3-arylated 4-oxochromanes. This approach has advantages compared to previous biocatalytic arylation protocols that use fungal laccases under slightly acidic conditions to allow a significant decrease in reaction time with improved yields and maintained regio- and diastereoselectivity. Furthermore, a successful diastereoselective, consecutive one-pot approach with the use of a hydrogenation flow system combined with the laccase-catalysed arylation was performed. Finally, the general utility of this enzyme as a superior biocatalyst for Michael additions using several nucleophiles was demonstrated. The corresponding starting material was obtained in a straightforward esterification/hydrogenation process with the latter accomplished by using the flow system.
Laccase-catalysed α-arylation of cyclic β-dicarbonyl compounds
Pietruszka, Joerg,Wang, Chuan
, p. 2402 - 2409 (2013/02/21)
In this protocol we described an environmentally friendly synthesis of α-arylated cyclic β-dicarbonyl compounds employing various catechols as precursors through an oxidation/Michael addition sequence. The process proceeded under the catalysis of a commercially available laccase at room temperature with the use of aerial oxygen as the oxidant affording the products in moderate to excellent yields (36-96%). Furthermore, a highly functionalized cyclopentane bearing an all-carbon quaternary stereogenic centre was synthesized through the arylation in excellent diastereoselectivity (dr > 99 : 1, 95% ee).
