Diastereo- and Enantioselective Construction of gamma-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita-Baylis-Hillman Acetates

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	Diastereo- and Enantioselective Construction of gamma-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita-Baylis-Hillman Acetates
	Wei Y(魏音) ; Ma GN(马光宁) ; Shi M(施敏)
刊名	Eur. J. Org. Chem.
	2011
期号	26 页码:5146-5155
其他题名	手性膦催化的MBH醋酸酯的烯丙基烷基化反应-高非对映和对映选择性地构建gama-环丁内酯
通讯作者	施敏
英文摘要	A series of multifunctional, chiral amide phosphane organocatalysts have been designed and synthesized for the allylic substitution of Morita-Baylis-Hillman (MBH) acetate with 2-trimethylsilyloxyfuran for butenolide synthesis. This reaction was achieved in good to excellent yield (42-98 %) and high ee (85-99 %) with respect to a wide range of substrates in absolute MeOH or CH(3)CN, using chiral amide phosphane organocatalysts with an amide moiety including an active proton. NMR tracing experiments identified the critical phosphonium intermediates involved in the catalytic cycles. Computational studies disclosed the origins of diastereo- and enantioselectivity, in particular, revealing that the active proton of the amide moiety is the critical factor for the catalyst to have high enantiofacial control.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/ejoc.201100704
语种	英语
WOS记录号	WOS:000295426800022
公开日期	2013-01-09
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/10430]
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	Wei Y,Ma GN,Shi M. Diastereo- and Enantioselective Construction of gamma-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita-Baylis-Hillman Acetates[J]. Eur. J. Org. Chem.,2011(26):5146-5155.
APA	Wei Y,Ma GN,&Shi M.(2011).Diastereo- and Enantioselective Construction of gamma-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita-Baylis-Hillman Acetates.Eur. J. Org. Chem.(26),5146-5155.
MLA	Wei Y,et al."Diastereo- and Enantioselective Construction of gamma-Butenolides through Chiral Phosphane-Catalyzed Allylic Alkylation of Morita-Baylis-Hillman Acetates".Eur. J. Org. Chem. .26(2011):5146-5155.