Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain

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	Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain
	Du HF(杜海峰) ; Zhao DB(赵东波) ; Ding KL(丁奎岭)
刊名	Chem.-Eur. J.
	2004
卷号	10 期号:23 页码:5964-5970
ISSN号	0947-6539
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
通讯作者	丁奎岭
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
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/chem.200400515
语种	英语
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17781]
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	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.
APA	杜海峰,赵东波,&丁奎岭.(2004).Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain.Chem.-Eur. J.,10(23),5964-5970.
MLA	杜海峰,et al."Enantioselective catalysis of hetero-Diels-Alder reaction between Brassard’s diene and aldehydes by hydrogenation bonding activation: One-step synthesis of (S)-(+)-dihydrokawain".Chem.-Eur. J. 10.23(2004):5964-5970.