| New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction | |
| Department | OSSO国家重点实验室 |
| Zheng LS(郑龙生)1; Li L(李莉)1; Yang KF(杨科芳)1; Zheng ZJ(郑战江)1; Xiao XQ(效旭琼)1; Xu LW(徐利文)1,2; Xu LW(徐利文) | |
| 2013 | |
| Source Publication | Tetrahedron
 |
| ISSN | 0040-4020 |
| Volume | 69Issue:41Pages:8777-8784 |
| Abstract | A new family of C2-axially chiral monophosphines (Ar-NNPs) from Ar-BINMOLs was developed for silvercatalyzed asymmetric vinylogous Mannich reaction of (furan-2-yloxy)trimethylsilane with aromatic aldimines. It was found that the enantioselective vinylogous Mannich-type reactions of trimethylsiloxyfuran with aldimines are catalyzed efficiently by silver(I) complexes of the Ar-BINMOL-derived chiral monophosphine. This procedure displays wide aldimine versatility, excellent yields (up to 99% isolated yields), moderate to good enantioselectivity (up to 78%ee) and exceptional diastereoselectivity (>99:1 dr) in most cases examined. The molecular structure of silveremonophosphine complex was confirmed by X-ray analysis and revealed that the benzyl group on chiral monophosphine provided dual function with weak silver-π/π-π stacking and steric repulsion to favour the diastereoselective Re-nucleophilic addition of siloxyfuran to imine. |
| Keyword | Silver Ar-binmol Phosphine Vinylogous Mannich Reaction Asymmetric Catalysis |
| Subject Area | 物理化学与绿色催化 |
| DOI | 10.1016/j.tet.2013.07.105 |
| Funding Organization | the National Natural Science Foundation of China (NSFC, Nos. 21173064;51203037);Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014);Zhejiang Provincial Natural Science Foundation of China (Q12B020037) |
| Indexed By | SCI |
| If | 2.817 |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/4871 |
| 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 |
| Recommended Citation GB/T 7714 | Zheng LS,Li L,Yang KF,et al. New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction[J]. Tetrahedron,2013,69(41):8777-8784. |
| APA | Zheng LS.,Li L.,Yang KF.,Zheng ZJ.,Xiao XQ.,...&徐利文.(2013).New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction.Tetrahedron,69(41),8777-8784. |
| MLA | Zheng LS,et al."New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction".Tetrahedron 69.41(2013):8777-8784. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| Tetrahedron 69 (2013（825KB） | 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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