enantioselective biaryl coupling catalyzed by enzymes

1,1′-联萘衍生物作为高立体选择性反应的手性诱导剂已广泛应用于有机合成中。通过光学拆分外消旋化合物、分子间Ullmann偶联、亲核芳香取代、2-萘酚与铜胺配合物氧化二聚化或电催化氧化偶联制备了对映体纯度高的二萘基衍生物。近年来，我们发现茶树细胞培养物是过氧化物酶（POD）的有效来源。我们建立了高POD活性的中华香椿细胞培养体系，并利用中华香椿细胞培养对映选择性氧化偶联2-萘酚衍生物。通过高POD活性的中华香椿细胞培养，实现了2-萘酚衍生物的对映选择性氧化偶联。值得注意的是，对于难以进行对映选择性氧化偶联反应的简单底物，如2-萘酚（CY 47%, OY 59%），获得了中等至良好的ee值。

1,1'-Binaphthalene derivatives have been widely used in organic synthesis as chirality inducers for highly stereoselective reactions. Enantiomerically pure binaphthyl derivatives have been prepared by optical resolution of racemic compounds, an intermolecular Ullmann coupling, a nucleophilic aromatic substitution, an oxidative dimerization of 2-naphthols with copper amine complexes as oxidant or electrocatalytic oxidative coupling. Recently we have found that camellia sinensis cell culture is an efficient source of peroxidase (POD) enzymes. We have established C. sinensis cell culture systems with high POD activity and applied enantioselective oxidative coupling of 2-naphthol derivatives by C. sinensis cell culture. A novel enantioselective oxidative coupling of 2-naphthol derivatives by C. sinensis cell culture with high POD activity can be achieved in this work. It is noteworthy that moderate to good ee values were obtained for simple substrates such as 2-naphthol (CY 47%, OY 59%) that are difficult substrates for enantioselective oxidative coupling reaction.