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学科主题: 有机化学
题名: Enantioselective synthesis of vinylcyclopropanes and vinylepoxides mediated by camphor-derived sulfur ylides: Rationale of enantioselectivity, scope, and limitation
其他题名: Enantioselective synthesis of vinylcyclopropanes and vinylepoxides mediated by camphor-derived sulfur ylides: Rationale of enantioselectivity, scope, and limitation
作者: Deng XM(邓贤明) ; Cai P(蔡萍) ; Sun XL(孙秀丽) ; Liao WW(寮渭巍) ; Li K(李凯) ; Tang Y(唐勇) ; Wu YD(吴云东) ; Dai LX(戴立信)
通讯作者: 唐勇
刊名: J. Am. Chem. Soc.
发表日期: 2006
卷: 128, 期:30, 页:9730-9740
收录类别: SCI
部门归属: 上海有机所
英文摘要: By a sidearm approach, camphor-derived sulfur ylides 1 were designed and synthesized for the cyclopropanation of electron-deficient alkenes and epoxidation of aldehydes. Under the optimal conditions, the exo-type sulfonium salts 4a and 4b reacted with, beta-aryl-alpha, beta-unsaturated esters, amides, ketones, and nitriles to give 1,3-disubstituted-2-vinylcyclopropanes with high diastereoselectivities and enantioselectivities. When the endo-type sulfonium salts 5a and 5b were used, the diastereoselectivities were not changed, whereas the absolute configurations of the products became the opposite to those of the reactions of 4a and 4b. An ylide cyclopropanation of chalcone derivatives with phenylvinyl bromide in the presence of catalytic amount of chiral sulfonium salts 4b and 5b has been developed. The sidearmed hydroxyl group was found to play a key role in the control of enantioselectivity and diastereoselectivity. The origins of the high diastereoselectivity and enantioselectivity were also studied by density functional theory calculations, which reveal the importance of the hydrogen-bonding between the sidearmed hydroxyl group and the substrate in determining the diastereoselectivity and enantioselectivity. The ylides 1 were also successfully applied for the epoxidation of aromatic aldehydes.
语种: 英语
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WOS记录号: WOS:000239278600049
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/15927
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:
Deng XM,Cai P,Sun XL,et al. Enantioselective synthesis of vinylcyclopropanes and vinylepoxides mediated by camphor-derived sulfur ylides: Rationale of enantioselectivity, scope, and limitation[J]. J. Am. Chem. Soc.,2006,128(30):9730-9740.
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