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学科主题: 金属有机化学
题名: Asymmetric Baeyer-Villiger Oxidation of 2,3-and 2,3,4-Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H2O2 as the Oxidant
其他题名: 手性膦酸催化双氧水为氧化剂的2,3-双取代外消旋环丁酮以及2,3,4-三取代环丁酮的不对称BV氧化反应
作者: Xu SM(徐森苗) ; Wang Z(王正) ; Zhang XM(张绪穆) ; Ding KL(丁奎岭)
通讯作者: 丁奎岭
刊名: Eur. J. Org. Chem.
发表日期: 2011-01-01
期: 1, 页:110-116
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 新泽西州立大学
英文摘要: Catalytic asymmetric Baeyer-Villiger (B-V) oxidation of 2,3,4-trisubstituted cyclobutanone (4) has been realized by the catalysis of a 1,1'-bi-2-naphthol (BINOL)-derived chiral phosphoric acid (1j), which contains bulky 2,4,6-triisopropyl phenyl groups at the 3,3'-positions of the BINOL backbone, using 30 % aqueous H2O2 as the oxidant, affording the corresponding gamma-lactone (5) in 99% yield with 95 % ee. In a divergent kinetic resolution of racemic 2,3-disubstituted bicyclic cyclobutanones (6) through asymmetric B-V oxidation, the chiral phosphoric acid 1p demonstrated excellent catalytic performance, giving a range of regioisomeric chiral lactones in a normal lactone (nl)/abnormal lactone (al) ratio of up to 2.1:1, with up to 99% ee in the al product. It was found that fine tuning of the stereoelectronic properties of the backbone in chiral phosphoric acids is critically important for attaining high levels of enantioselectivity in the catalysis of B-V reactions of different type of cyclobutanones. The present work has provided a convenient approach to the synthesis of a variety of optically active chiral gamma-lactones.
语种: 英语
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WOS记录号: WOS:000286774900012
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17889
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
Xu SM,Wang Z,Zhang XM,et al. Asymmetric Baeyer-Villiger Oxidation of 2,3-and 2,3,4-Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H2O2 as the Oxidant[J]. Eur. J. Org. Chem.,2011(1):110-116.
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