Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides
文献类型：期刊论文
| 作者 | Yang W(杨伟)1; Jiang KZ(蒋可志)1; Lu X(鲁幸)1; Yang HM(杨化萌)1; Li L(李莉)1; Lu YX(卢一新)3,4; Xu LW(徐利文)1,2 |
| 刊名 | Chemistry - An Asian Journal
 |
| 出版日期 | 2013 |
| 卷号 | 8期号:6页码:1182-1190 |
| ISSN号 | 1861-4728 |
| 关键词 | aldehydes Michael addition molecular assembly organocatalysis supramolecular chemistry |
| 通讯作者 | 徐利文 |
| 英文摘要 | A combined catalyst system of a cinchonidine-derived primary amine and triphenylphosphine (CDNH2/PPh3) exhibited high catalytic performance in the Michael reaction of aldehydes with maleimides, thereby affording the corresponding functionalized aldehydes in excellent yields (up to 99%) and enantioselectivities (>99% ee). More interestingly, the significance of the phosphine in enhancing the enantioselectivities in the chiral-primary-amine-catalyzed Michael reaction was revealed. Furthermore, we explored the origin of the reaction mechanism in the Michael addition promoted by the dual organocatalytic system. On the basis of experimental results and spectroscopic analysis, such as UV/Vis, fluorescence emission (FL), NMR, and circular dichroism (CD) spectroscopy, as well as ESI-MS, we found that the molecular assembly of phosphine and primary amine played a crucial role in this enantioselective reaction, in which a possible supramolecular complex was formed as an effective chiral catalyst through noncovalent molecular interactions of a cinchona alkaloid-derived primary amine with triphenylphosphine. |
| 学科主题 | 物理化学与绿色催化 |
| 资助信息 | the National Natural Science Foundation of China (NSFC, 20973051;21173064);the Zhejiang Provincial Natural Science Foundation of China (ZPNSFC, Q12B020037);the Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014) |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000319424300017 |
| 公开日期 | 2013-12-24 |
| 源URL | [http://210.77.64.217/handle/362003/4865]  |
| 专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
| 作者单位 | 1.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 3.Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore 4.Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117543, Singapore |
| 推荐引用方式 GB/T 7714 | Yang W,Jiang KZ,Lu X,et al. Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides[J]. Chemistry - An Asian Journal,2013,8(6):1182-1190. |
| APA | Yang W.,Jiang KZ.,Lu X.,Yang HM.,Li L.,...&Xu LW.(2013).Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides.Chemistry - An Asian Journal,8(6),1182-1190. |
| MLA | Yang W,et al."Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides".Chemistry - An Asian Journal 8.6(2013):1182-1190. |
入库方式： OAI收割
来源：兰州化学物理研究所
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