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	Chiral phosphine lewis bases catalyzed asymmetric aza-Baylis-Hiliman reaction of N-sulfonated imines with activated olefins
	Shi M(施敏) ; Chen LH(陈连辉) ; Li CQ(李超群)
刊名	J. Am. Chem. Soc.
	2005
卷号	127期号:11页码:3790-3800
其他题名	手性膦化合物催化的不对称杂Baylis–Hillman Reaction
通讯作者	施敏
英文摘要	In 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.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/ja0447255
语种	英语
WOS记录号	WOS:000227738700045
公开日期	2013-01-09
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/10000]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 GB/T 7714	Shi M,Chen LH,Li CQ. 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.(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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