Synthesis and Crystal Structure of 4-Oxo-3-aza-tricyclo-[184.108.40.206~(2,5)]undecane-9-carb-oxylic Acid Methyl Ester
- 化学化工－已发表论文 
[中文文摘]以2-金刚烷酮为起始原料,通过烯烃与氯磺酰异氰酸酯的[2+2]环加成等5步反应合成了新型双环β-内酰胺类化合物5.采用1H NMR,IR和MS等手段对所得化合物的结构进行了表征.此外,还通过将化合物5酰化并采用X射线单晶衍射分析方法进一步测定了化合物5的空间立体结构.结果表明,烯烃3与氯磺酰异氰酸酯的[2+2]环加成反应具有高度的立体选择性和区域选择性.[英文文摘]Since the [2+2] cycloaddition of chlorosulfonyl isocyanate(CSI) with an alkene is a very effective method for the synthesis of β-lactams in organic synthesis.In this paper,a new type bicyclic β-lactam compound was synthesized starting from 2-adamantanone employing the [2+2]cycloaddition strategy.The compound 4-oxo-3-aza-tricyclo-[5.3.1.02,5]undecane-9-carb-oxylic 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 1H NMR, IR spectra and MS techniques, and the structure of 4-oxo-3-aza-tr icyclo-[ 220.127.116.11 2,5] undecane-9-carb-oxylic acid methyl ester(5) was further determ ined by X-ray single crystal diffraction analysismethod 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 B-lactams.