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. |
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