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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
Shi M(施敏); Xu YM(徐永梅); Shi YL(时永灵); Shi M(施敏)
2005
发表期刊Chem.-Eur. J.
卷号11期号:6页码:1794-1802
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.
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
WOS记录号WOS:000227662900011
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被引频次:123[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/10002
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
Shi M,Xu YM,Shi YL,et al. 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.
APA Shi M,Xu YM,Shi YL,&施敏.(2005).Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines.Chem.-Eur. J.,11(6),1794-1802.
MLA Shi M,et al."Catalytic, asymmetric aza-Baylis-Hillman reaction of N-sulfonated imines with activated olefins by quinidine-derived chiral amines".Chem.-Eur. J. 11.6(2005):1794-1802.
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