Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes

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	Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes
	Shen H(沈浩) ; Yang KF(杨科芳) ; Shi ZH(史子惠) ; Jiang JX(蒋剑雄) ; Lai GQ(来国桥) ; Xu LW(徐利文)
刊名	Eur. J. Org. Chem.
	2011
页码	5031-5038
关键词	Asymmetric catalysis Organocatalysis Domino reactions Multicomponent reactions Silicon
ISSN号	1434-193X
通讯作者	徐利文
中文摘要	The one-pot, organocatalytic Hayashi sequential reaction (HSR) of β-nitroacrylate, aldehyde, toluenethiol, and ethyl 2- (diethoxyphosphoryl)acrylate allowed the synthesis of almost stereoisomerically pure, highly functionalized polysubstituted cyclohexanes with very high diastereo- and enantioselectivity (up to 99%ee). The one-pot synthesis consists of the tertiary amine modified diarylprolinol silyl ether-mediated asymmetric Michael reaction, a domino Michael reaction/ Horner–Wadsworth–Emmons reaction, and a sulfa- Michael reaction. In addition, we have also demonstrated an improved protocol for the domino oxa-Michael/aldol reactionof salicyladehydes with α,β-unsaturated aldehydes with recyclable tertiary amine-modified diarylprolinol silyl ether 3d as an effective organocatalyst, which results in the formation of chiral chromenes with good enantioselectivities (up to 94%ee). UV/Vis and CD spectroscopy provide a cross-validation method to elucidate the slight difference between electron-withdrawing 3d and diphenylprolinol silyl ether 3a, which can give indirect evidence for the enhancement of enantioselective induction with 3d in the above transformations.
学科主题	物理化学
收录类别	SCI
资助信息	the National Natural Science Foundation of China (NSFC, No. 20973051);Program for ExcellentYoung Teachers in Hangzhou Normal University (HNUEYT);Hangzhou Science and Technology Program (20090231T03)
语种	英语
WOS记录号	WOS:000295426800008
公开日期	2012-09-20
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/376]
专题	兰州化学物理研究所_OSSO国家重点实验室
推荐引用方式 GB/T 7714	Shen H,Yang KF,Shi ZH,et al. Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes[J]. Eur. J. Org. Chem.,2011:5031-5038.
APA	沈浩,杨科芳,史子惠,蒋剑雄,来国桥,&徐利文.(2011).Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes.Eur. J. Org. Chem.,5031-5038.
MLA	沈浩,et al."Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes".Eur. J. Org. Chem. (2011):5031-5038.