Chiral phosphite ligands derived from L-(+)-tartaric acid: synthesis and application in the Cu-catalyzed 1,4-conjugate addition of organozincs to cyclic enones
文献类型：期刊论文
| 作者 | Xing AP(刑爱萍)1,2; Bai CB(白翠冰)3; Wang LL(王来来)1
|
| 刊名 | Tetrahedron
 |
| 出版日期 | 2013 |
| 卷号 | 69期号:2页码:455-459 |
| 关键词 | Phosphite ligands Copper precursor Organozincs Cyclic enones Conjugate addition |
| ISSN号 | 0040-4020 |
| 通讯作者 | 王来来 |
| 英文摘要 | A new series of chiral phosphite ligands derived from readily available L-(＋)-tartaric acid and binaphthol derivatives were designed and prepared in convenient synthetic routes. These ligands were successfully employed in the Cu-catalyzed asymmetric conjugate addition of organozincs to cyclic enones. The ligands bearing (R)- and (S)-binaphthol and/or 3,3′-bis(trimethylsilyl)-2,2′-dihydroxy-1,1′-binaphthol afforded both enantiomers of the product in high yields and good enantioselectivities (up to 95% ee). The chiral organocopper reagent did exhibit high enantioselectivities for cyclic enones bearing different ring sizes. The stereochemically matched combination of L-(＋)-tartaric acid backbone and (R)-binaphthyl in ligand 1-N-benzylpyrrolidine-3,4-bis[(R)-1,10-binaphthyl-2,20-diyl]phosphite-L-tartaric acid was essential to afford 95% (R) ee for 3-ethylcyclopentanone, 95% ee (S) for 3-ethyl-cyclohexanone, and 63% ee (R) for 3-ethylcycloheptanone in ether as solvent, using (CuOTf)2﹒C6H6 as a catalytic precursor. Moreover, the sense of the enantio discrimination of the products was mainly determined by the configuration of the binaphthyl phosphite moieties. |
| 学科主题 | 物理化学与绿色催化 |
| 收录类别 | SCI |
| 资助信息 | the National Natural Science Foundation of China (Nos. 20343005;20473107;20673130;20773147;21073211;21174155) |
| 语种 | 英语 |
| WOS记录号 | WOS:000314371800002 |
| 公开日期 | 2013-12-03 |
| 源URL | [http://210.77.64.217/handle/362003/4282]  |
| 专题 | 兰州化学物理研究所_OSSO国家重点实验室 |
| 作者单位 | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 2.Chinese Acad Sci, Grad Univ, Beijing 100039, Peoples R China 3.NW Normal Univ, Coll Chem & Chem Engn, Key Lab Polymer Mat Gansu Prov, Lanzhou 730070, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xing AP,Bai CB,Wang LL. Chiral phosphite ligands derived from L-(+)-tartaric acid: synthesis and application in the Cu-catalyzed 1,4-conjugate addition of organozincs to cyclic enones[J]. Tetrahedron,2013,69(2):455-459. |
| APA | Xing AP,Bai CB,&Wang LL.(2013).Chiral phosphite ligands derived from L-(+)-tartaric acid: synthesis and application in the Cu-catalyzed 1,4-conjugate addition of organozincs to cyclic enones.Tetrahedron,69(2),455-459. |
| MLA | Xing AP,et al."Chiral phosphite ligands derived from L-(+)-tartaric acid: synthesis and application in the Cu-catalyzed 1,4-conjugate addition of organozincs to cyclic enones".Tetrahedron 69.2(2013):455-459. |
入库方式： OAI收割
来源：兰州化学物理研究所
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