Ilie Adriana, Harms Klaus, Reetz Manfred T
Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm-Platz 1 , 45470 Mülheim an der Ruhr , Germany.
Department of Chemistry , Philipps-Universität Marburg , Hans-Meerwein Str. 4 , 35032 Marburg , Germany.
J Org Chem. 2018 Jul 20;83(14):7504-7508. doi: 10.1021/acs.joc.7b02878. Epub 2018 Jan 23.
Chiral alcohols are important building blocks for the production of pharmaceuticals, catalytic access being possible by the use of enzymes, transition metal catalysts, or organocatalysts. Herein we report the use of cytochrome P450-BM3 mutants for the oxidative hydroxylation of 6-iodotetralone regio- and enantioselectively at C4 with formation of the ( R)-alcohol. This CH activation is not possible using modern synthetic catalysts. The synthetic utility of this valuable synthon was explored in palladium-catalyzed coupling reactions that occur in the absence of undesired racemization.
手性醇是药物生产的重要构建单元，可通过使用酶、过渡金属催化剂或有机催化剂实现催化合成。在此，我们报道了细胞色素P450-BM3突变体用于6-碘代四氢萘酮在C4位区域和对映选择性氧化羟基化反应，生成(R)-醇。使用现代合成催化剂无法实现这种碳氢键活化。在钯催化的偶联反应中探索了这种有价值合成子的合成效用，该反应不会发生不期望的外消旋化。
