| Recyclable Tertiary Amine Modified Diarylprolinol Ether as Aminocatalyst for the Sequential Asymmetric Synthesis of Functionalized Cyclohexanes and Chromenes | |
| Department | 羰基合成与选择氧化国家重点实验室 |
| 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) | |
| 2011 | |
| Source Publication | Eur. J. Org. Chem.
 |
| ISSN | 1434-193X |
| Pages | 5031-5038 |
| Abstract | 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. |
| Keyword | Asymmetric Catalysis Organocatalysis Domino Reactions Multicomponent Reactions Silicon |
| Subject Area | 物理化学 |
| Funding Organization | 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) |
| Indexed By | SCI |
| Language | 英语 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/376 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Xu LW(徐利文) |
| Recommended Citation 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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| 70-Eur. J. Org. Chem（367KB） | 开放获取 | License | View Application Full Text | |||
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