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学科主题: 金属有机化学
题名: A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione
其他题名: 光学纯手性螺[4,4]-1,6-壬二酮的实用不对称合成
作者: Han ZB(韩召斌) ; Wang Z(王正) ; Ding KL(丁奎岭)
通讯作者: 丁奎岭
刊名: Adv. Synth. Catal.
发表日期: 2011
卷: 353, 期:9, 页:1584-1590
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: A practical asymmetric synthesis of enantiopure spiro[4,4]nonane-1,6-dione, a valuable precursor for chiral ligand development, is reported. This synthetic strategy includes a kinetic resolution of the readily synthesized ketone precursor with a chiral quaternary carbon center by bioreduction with baker's yeast as the key step, followed by a hydroformylation, oxidation, esterification and Dieckmann cyclization reaction sequence to generate the spiro five-membered ring. It was found that the masking of the beta-ketone carbonyl group of enantiopure ethyl 1-allyl-2-oxocyclopentanecarboxylate via formation of a ketal with 1,3-diol derivative is necessary during the process of Dieckmann condensation in order to prevent its racemization under basic conditions. This method allows the gram-scale preparation of both enantiomers of spiro[4,4]nonane-1,6-dione (1) with excellent enantiopurities (up to >99% ee) in the overall yields of 54% [(R)-1] and 42% [(S)-1], respectively. The practicality of the present synthetic procedure has provided a fundamental platform for the development of spiro[4,4]nonane-1,6-dione-based chiral chemistry.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000292848200029
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17893
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:
Han ZB,Wang Z,Ding KL. A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione[J]. Adv. Synth. Catal.,2011,353(9):1584-1590.
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