1397495-68-9Relevant academic research and scientific papers
Tyrosinases in Organic Chemistry: A Versatile Tool for the α-Arylation of β-Dicarbonyl Compounds
Krug, Roxanne,Schr?der, Dennis,Gebauer, Jan,Sulji?, Sanel,Morimoto, Yuma,Fujieda, Nobutaka,Itoh, Shinobu,Pietruszka, J?rg
, p. 1789 - 1796 (2018)
A tyrosinase-mediated arylation towards a variety of different building blocks is presented. Utilizing phenol or simple substituted phenols, the corresponding quinones are synthesized in a two-step procedure by an enzyme-catalyzed oxidation (tyrosinase from Aspergillus oryzae). The activated intermediates undergo a 1,4-addition with selected β-dicarbonyl compounds. Starting from phenol, yields of isolated product for the hydroxylation-oxidation-arylation sequence range from 43–77 %, whereas substituted acceptors provided 9–55 %, only. Different substitution patterns on phenol revealed that electron donating functionalities are preferentially accepted to electron withdrawing ones, whereas ortho-substituted phenols are not accepted at all.
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).
