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	Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[5310(2,5)]undecane-9-carb-oxylic Acid Methyl Ester
	Liang Guo-Juan ; Chen An-Qi ; Chen AQ(陈安齐)
	2011-02-10
关键词	CHLOROSULFONYL ISOCYANATE DERIVATIVES
英文摘要	Since the [2 + 2] cycloaddition of chlorosulfonyl isocyanate (CSI) with an alkene is a very effective method for the synthesis of beta-lactams in organic synthesis. In this paper, a new type bicyclic beta-lactam compound was synthesized starting from 2-adamantanone employing the [2 + 2] cycloaddition strategy. The compound 4-oxo-3-aza-tricyclo-[5. 3. 1. 0(2, 5)]undecane-9-carb-oxylc acid methyl ester (5) was synthesized in five steps in 47. 5% overall yield including esterification of the carboxy group, [2 + 2] cycloaddition of the alkene 3 with CSI. Their structures were characterized by means of H-1 NMR, IR spectra and MS techniques, and the structure of 4-oxo-3-aza-tricyclo-[5. 3. 1. 0(2,5)]undecane-9-carb-oxylic acid methyl ester (5) was further determined by X-ray single crystal diffraction analysis method after the acylation reaction. The results indicate that the [2 + 2] cycloaddition of cyclic alkene 3 with chlorosulfonyl isocyanate proceeded with excellent regio-and stereo-selectivity. This work provides a good option for the chiral synthesis of beta-lactams.
语种	英语
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/64087]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Liang Guo-Juan,Chen An-Qi,Chen AQ. Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[5310(2,5)]undecane-9-carb-oxylic Acid Methyl Ester[J],2011.
APA	Liang Guo-Juan,Chen An-Qi,&陈安齐.(2011).Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[5310(2,5)]undecane-9-carb-oxylic Acid Methyl Ester..
MLA	Liang Guo-Juan,et al."Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[5310(2,5)]undecane-9-carb-oxylic Acid Methyl Ester".(2011).

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