Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones

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	Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones
	Yin BL(尹标林) ; Wu YL(吴毓林) ; Lai JQ(赖景强)
刊名	Eur. J. Org. Chem.
	2009
期号	16 页码:2695-2699
ISSN号	1434-193X
其他题名	从呋喃二醇和螺缩环到环戊烯酮的新转化
通讯作者	尹标林
英文摘要	Two acid-catalyzed conversions of furandiols 8 and its dehydration spiroacetalized products 9 into oxabicyclic cyclopentenones 10 in good to excellent yields are reported. To disclose the mechanism of these conversions, the fact that H2O catalyzes the conversion of 9 into 10 is presented and intermediates 9k and 20i have been structurally verified. In addition, two other related conversions of spiroacetal enol ethers 11 and 14 derived from 8 into cyclopentenones are presented, for which an intramolecular aldol reaction is the key step. On the basis of these results, we propose that these conversions occur through an aldol condensation step instead of electrocyclization of the 4 pi-electron system, which was previously reported. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
学科主题	生命有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/ejoc.200900129
语种	英语
WOS记录号	WOS:000266525100012
公开日期	2013-01-17
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/14114]
专题	上海有机化学研究所_生命有机化学国家重点实验室
推荐引用方式 GB/T 7714	Yin BL,Wu YL,Lai JQ. Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones[J]. Eur. J. Org. Chem.,2009(16):2695-2699.
APA	尹标林,吴毓林,&赖景强.(2009).Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones.Eur. J. Org. Chem.(16),2695-2699.
MLA	尹标林,et al."Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones".Eur. J. Org. Chem. .16(2009):2695-2699.