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Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins
Alternative Title手性膦化合物催化的不对称杂Baylis–Hillman Reaction
Shi M(施敏); Chen LH(陈连辉); Li CQ(李超群); Shi M(施敏)
2005
Source PublicationJ. Am. Chem. Soc.
Volume127Issue:11Pages:3790-3800
AbstractIn the aza-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides and others) with methyl vinyl ketone, ethyl vinyl ketone, and acrolein, we found that, in the presence of a catalytic amount of chiral phosphine Lewis base such as (R)-2'-diphenylphosphanyl[1, 1']binaphthalenyl-2-ol LB1 (10 mol %) and molecular sieve 4A, the corresponding aza-Baylis-Hillman adducts could be obtained in good yields with good to high ee (70-95% ee) at low temperature (∼-30 to -20 ° C) or at room temperature in THF, respectively. In CH2Cl2 upon heating at 40 ° C, the aza-Baylis-Hillman reaction of N-sulfonated imines with phenyl acrylate or naphthyl acrylate gave the adducts in good to high yields (60-97%) with moderate ee (52-77%). The mechanistic insight has been investigated by P-31 and H-1 NMR spectroscopic measurements. The key enolate intermediate, which has been stabilized by intramolecular hydrogen bonding, has been observed by P-31 and H-1 NMR spectroscopy. An effective bifunctional Lewis base and Bronsted acid phosphine Lewis base system has been disclosed in this catalytic, asymmetric aza-Baylis-Hillman reaction.
Subject Area金属有机化学
Department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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Indexed BySCI
Language英语
WOS IDWOS:000227738700045
Citation statistics
Cited Times:309[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/10000
Collection金属有机化学国家重点实验室
Corresponding AuthorShi M(施敏)
Recommended Citation
GB/T 7714
Shi M,Chen LH,Li CQ,et al. Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins[J]. J. Am. Chem. Soc.,2005,127(11):3790-3800.
APA Shi M,Chen LH,Li CQ,&施敏.(2005).Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins.J. Am. Chem. Soc.,127(11),3790-3800.
MLA Shi M,et al."Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins".J. Am. Chem. Soc. 127.11(2005):3790-3800.
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