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Asymmetric Baeyer-Villiger Oxidation of 2,3-and 2,3,4-Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H2O2 as the Oxidant

文献类型:期刊论文

作者Xu SM(徐森苗) ; Wang Z(王正) ; Zhang XM(张绪穆) ; Ding KL(丁奎岭)
刊名Eur. J. Org. Chem.
出版日期2011
期号1页码:110-116
ISSN号1434-193X
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
通讯作者丁奎岭
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.
学科主题金属有机化学
收录类别SCI
原文出处http://dx.doi.org/10.1002/ejoc.201001130
语种英语
WOS记录号WOS:000286774900012
公开日期2013-02-22
源URL[http://202.127.28.38/handle/331003/17889]  
专题上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式
GB/T 7714
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.
APA 徐森苗,王正,张绪穆,&丁奎岭.(2011).Asymmetric Baeyer-Villiger Oxidation of 2,3-and 2,3,4-Substituted Cyclobutanones Catalyzed by Chiral Phosphoric Acids with Aqueous H2O2 as the Oxidant.Eur. J. Org. Chem.(1),110-116.
MLA 徐森苗,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".Eur. J. Org. Chem. .1(2011):110-116.

入库方式: OAI收割

来源:上海有机化学研究所

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