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学科主题: 金属有机化学
题名: Dramatically synergetic effect of carboxylic acid additive on tridentate titanium catalyzed enantioselective Hetero-Diels-Alder reaction: additive acceleration and nonlinear effect
其他题名: 三齿钛络合物催化的不对称杂-DA反应中羧酸添加物的协同效应: 添加物加速与非线性效应
作者: Yuan Y(袁宇) ; Long J(龙江) ; Sun J(孙杰) ; Ding KL(丁奎岭)
通讯作者: 丁奎岭
刊名: Chem.-Eur. J.
发表日期: 2002
卷: 8, 期:21, 页:5033-5042
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所金属有机化学开放实验室
英文摘要: This paper describes the successful development of a group of highly efficient chiral tridentate titanium catalysts for hetereo-Diels-Alder reaction of Danishefsky's diene and a variety of aldehydes through ligand and additive diversity. Dramatically synergetic effect of carboxylic acid additives and influence of substituent in chiral schiff base ligands on the enantioselectivities of the reaction are reported. It was found that a chiral durg naproxen (A21) was a highly efficient additive for Ti-catalyzed HAD reaction, affording 2-substituted. 2,3-dihydro-4H-pyran-4-one in up to 97% ee and >99% yields. Quantitative study of the effect of chiral carboxylic acid A21 revealed that the reaction could be accelerated by one order of magnitude. Another interesting feature of present catalytic system is the existence of significant positive nonlinear effect, which indicates that the heterochiral Schiff base-titanium complexes may have higher stability than their homochiral counterparts. As a result, the homochiral Schiff base-titanium complexes with higher ee than that of starting ligand will react with carboxylic acid additive to form the more active species and predominate the catalytic process. The isolation and characterization of stable heterochiral ((±)-L1)^2 Ti complex has also been successful, which strongly supported the explanation for positive nonlinear effect observed in the catalytic system.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000179155400023
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17749
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:
Yuan Y,Long J,Sun J,et al. Dramatically synergetic effect of carboxylic acid additive on tridentate titanium catalyzed enantioselective Hetero-Diels-Alder reaction: additive acceleration and nonlinear effect[J]. Chem.-Eur. J.,2002,8(21):5033-5042.
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