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学科主题: 金属有机化学
题名: Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines
其他题名: 奎宁丁衍生的手性胺类化合物催化的不对称杂Baylis–Hillman Reaction
作者: Shi M(施敏) ; Xu YM(徐永梅) ; Shi YL(时永灵)
通讯作者: 施敏
刊名: Chem.-Eur. J.
发表日期: 2005
卷: 11, 期:6, 页:1794-1802
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: The chiral nitrogen Lewis base, tricyclic cinchona alkaloid derivative TQO, is an effective promoter in the catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines Ar-CH=NR' 1 (R' = Ts, Ms, Ns, SES) with various activated olefins such as methyl vinyl ketone (MVK), ethyl vinyl ketone (EVK), acrolein, methyl acrylate, phenyl acrylate, or alpha-naphthyl acrylate to give the corresponding adducts in moderate to good yields with good to high ee (up to 99%) at -30 degrees C or 45 degrees C in various solvents, including DMF/MeCN (1:1, v/v). The first such reaction of 1 with the simplest Michael acceptor MVK and methyl acrylate has been achieved with excellent enantioselectivity. The adducts derived from MVK and EVK had the opposite absolute configuration to those from acrolein, methyl acrylate, phenyl acrylate, and alpha-naphthyl acrylate. A plausible mechanism has been proposed on the basis of previous reports and the authors' investigations. An effective bifunctional chiral nitrogen Lewis base-Bronsted acid system has been revealed in this type of aza-Baylis-Hillman reaction.
语种: 英语
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WOS记录号: WOS:000227662900011
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/10002
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:
Shi M,Xu YM,Shi YL. Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines[J]. Chem.-Eur. J.,2005,11(6):1794-1802.
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