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学科主题: 金属有机化学
题名: Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain
其他题名: 通过氢键活化的Brassard二烯与醛的不对称杂DA反应:一步合成(S)-(+)-dihydrokawain
作者: Du HF(杜海峰) ; Zhao DB(赵东波) ; Ding KL(丁奎岭)
通讯作者: 丁奎岭
刊名: Chem.-Eur. J.
发表日期: 2004-01-01T00:00:00Z
卷: 10, 期:23, 页:5964-5970
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: The first catalytic enantioselective hetero-Diels-Alder reaction between Brassard's diene and aldehydes has been achieved through hydrogen-bonding activation using TADDOL derivatives as catalysts to afford the corresponding delta-lactone derivatives in moderate-to-good yields and with high enantioselectivities (up to 91 % ee). The reactions can be carried out either under solvent-free conditions or in toluene. On the basis of the absolute configurations of the products and the hydrogen-bonding interaction pattern between TADDOL (alpha,alpha,alpha',alpha'-tetraaryl-1,3-dioxolan-4,5-dimethanol) and the carbonyl group disclosed by X-ray diffraction analysis, a possible mechanism for the catalytic reaction has been proposed. To demonstrate the usefulness of the methodology, a natural product, (S)-(+)-dihydrokawain, has also been prepared in 50 % isolated yield and with 69 % enantioselectivity in one step starting from 3-phenylpropionaldehyde by using this methodology. Therefore, this catalytic system is one of the most direct approaches to the construction of delta-lactone units, which will make the methodology very attractive for the synthesis of a variety of biologically important compounds and natural products. Author Keywords: asymmetric catalysis; hetero-Diels-Alder reactions; hydrogen-bonding activation; lactones; organo catalysis; TADDOL
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17781
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:
Du HF,Zhao DB,Ding KL. Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain[J]. Chem.-Eur. J.,2004,10(23):5964-5970.
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