A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione

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	A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione
	Han ZB(韩召斌) ; Wang Z(王正) ; Ding KL(丁奎岭)
刊名	Adv. Synth. Catal.
	2011
卷号	353 期号:9 页码:1584-1590
ISSN号	1615-4150
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
通讯作者	丁奎岭
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.
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/adsc.201100089
语种	英语
WOS记录号	WOS:000292848200029
公开日期	2013-02-22
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/17893]
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	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.
APA	韩召斌,王正,&丁奎岭.(2011).A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione.Adv. Synth. Catal.,353(9),1584-1590.
MLA	韩召斌,et al."A Practical Asymmetric Synthesis of Enantiopure Spiro[4,4]nonane-1,6-dione".Adv. Synth. Catal. 353.9(2011):1584-1590.