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学科主题: 生命有机化学
题名: Novel Conversions of Furandiols and Spiroacetal Enol Ethers into Cyclopentenones: Implications of the Isomerization Mechanism of 2-Furylcarbinois into Cyclopentenones
其他题名: 从呋喃二醇和螺缩环到环戊烯酮的新转化
作者: Yin BL(尹标林) ; Wu YL(吴毓林) ; Lai JQ(赖景强)
通讯作者: 尹标林
刊名: Eur. J. Org. Chem.
发表日期: 2009
期: 16, 页:2695-2699
收录类别: SCI
部门归属: 华南理工大学; 上海有机所
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)
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000266525100012
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/14114
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
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.
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