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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
Liu YH(刘英豪); Chen LH(陈连辉); Shi M(施敏); Shi M(施敏)
2006
发表期刊Adv. Synth. Catal.
卷号348期号:7-8页码:973-979
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.
学科领域金属有机化学
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
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收录类别SCI
语种英语
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/10042
专题金属有机化学国家重点实验室
通讯作者Shi M(施敏)
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GB/T 7714
Liu YH,Chen LH,Shi M,et al. 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.
APA Liu YH,Chen LH,Shi M,&施敏.(2006).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.Adv. Synth. Catal.,348(7-8),973-979.
MLA Liu YH,et al."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".Adv. Synth. Catal. 348.7-8(2006):973-979.
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