enantioselective biaryl coupling catalyzed by enzymes

酶催化的对映选择性联芳基偶联

• 批准号: 12672057
• 负责人: TAKEMOTO Masumi
• 金额: $ 2.05万
• 依托单位: University of Shizuoka
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2000
• 资助国家: 日本
• 起止时间: 2000 至 2002
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-12672057/
• 关键词: enzymes; plant cell culture; Camellia sinensis cell culture; atropisomer; biaryl coupling; 2-naphthol; peroxidase; oxidative coupling

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.

1，1 '-联萘衍生物作为手性诱导剂在有机合成中有着广泛的应用。通过外消旋化合物的光学拆分、分子间Ullmann偶联、芳香亲核取代、以铜胺络合物为氧化剂的2-萘酚氧化二聚反应或电催化氧化偶联反应制备了对映体纯的联萘衍生物。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。我们已经建立了C. sinensis细胞培养体系，并应用C.细胞培养利用C.本工作可获得高POD活性的中华绒螯蟹细胞培养物。值得注意的是，对于简单底物如2-萘酚（CY 47%，OY 59%）获得了中等至良好的ee值，所述简单底物对于对映选择性氧化偶联反应是困难的底物。

项目成果

Masumi Takemoto, Yuki Suzuki, Kiyoshi Tanaka: "Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by Camellia sinensis cell culture"Tetrahedron Lett.. 43. 8499-8501 (2002)

Masumi Takemoto、Yuki Suzuki、Kiyoshi Tanaka：“茶树细胞培养物催化的 2-萘酚衍生物的对映选择性氧化偶联”Tetrahedron Lett.. 43. 8499-8501 (2002)

Msumi Takemoto., Yuki Suzuki., and Kiyoshi Tanaka.: "Enantioselective oxidative coupling of 2-naphthol derivatives catalyzed by Camellia sinensis cell culture"Tetrahedron Lett.. 43. 8499-8501 (2002)

Msumi Takemoto.、Yuki Suzuki.、Kiyoshi Tanaka.：“茶树细胞培养物催化的 2-萘酚衍生物的对映选择性氧化偶联”Tetrahedron Lett.. 43. 8499-8501 (2002)

Masumi Tkemoto: "Enantioselective Oxidative Coupling of 2-NaphtholDerivatives Catalyzed by Camellia Sinensis Cell Culture"Tetrahedron Lett.. 43. 8499-8501 (2002)

Masumi Tkemoto：“茶树细胞培养物催化的 2-萘酚衍生物的对映选择性氧化偶联”Tetrahedron Lett.. 43. 8499-8501 (2002)