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学科主题: 金属有机化学
题名: Asymmetric aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with activated olefins catalyzed by chiral phosphine Lewis bases bearing multiple phenol groups phosphine; Lewis base; organocatalysts; phenol groups; N-sulfonated imines
其他题名: 具有多个酚羟基的手性膦化合物在催化磺酰亚胺和活化烯的aza-Baylis-Hillman反应中的应用
作者: Liu YH(刘英豪) ; Chen LH(陈连辉) ; Shi M(施敏)
通讯作者: 施敏
刊名: Adv. Synth. Catal.
发表日期: 2006
卷: 348, 期:7-8, 页:973-979
收录类别: SCI
部门归属: 中科院上海有机所金属有机化学国家重点实验室
英文摘要: In the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides) with methyl vinyl ketone (MVK), ethyl vinyl ketone (EVK), and acrolein, we found that. through the use of catalytic amounts of chiral phosphine Lewis bases bearing multiple phenol groups, the corresponding adducts could be obtained in good yields with > 90% ee at -20 degrees C or at room temperature in THE The mechanism of this process was investigated by P-31 NMR spectroscopic analysis. The phenoxide or the key enolate intermediate, which is stabilized by intramolecular hydrogen bonding with phenol groups, was observed by P-31 NMR spectroscopy. Thus, the most effective bifunctional LBBA (Lewis base and Bronsted acid) phosphine-Lewis base promoter system reported to date has been identified for such catalytic, asymmetric aza-Morita-Baylis-Hillman reactions.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/10042
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:
Liu YH,Chen LH,Shi M. Asymmetric aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with activated olefins catalyzed by chiral phosphine Lewis bases bearing multiple phenol groups phosphine; Lewis base; organocatalysts; phenol groups; N-sulfonated imines[J]. Adv. Synth. Catal.,2006,348(7-8):973-979.
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