| 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 | |
| Department | OSSO国家重点实验室 |
| 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; Xu LW(徐利文) | |
| 2013 | |
| Source Publication | Chemistry - An Asian Journal
 |
| ISSN | 1861-4728 |
| Volume | 8Issue:6Pages:1182-1190 |
| Abstract | 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. |
| Keyword | Aldehydes Michael Addition Molecular Assembly Organocatalysis Supramolecular Chemistry |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1002/asia.201300141 |
| Funding Organization | 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) |
| Indexed By | SCI |
| If | 3.935 |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/4865 |
| 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) |
| Affiliation | 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 |
| Recommended Citation 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.,...&徐利文.(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. |
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| File Name/Size | DocType | Version | Access | License | ||
| Chem. Asian J. 2013,（623KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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