4-dimethylaminopyridine-catalyzed dynamic kinetic resolution in asymmetric synthesis of p-chirogenic 1,3,2-oxazaphospholidine-2-oxides
文献类型：期刊论文
| 作者 | Wang, Lanlan1,2; Cao, Shanshan3; Du, Zhijun1; Wu, Qiang1,2; Bian, Zheng1; Kang, Chuanqing1; Gao, Lianxun1; Zhang, Jingping3 |
| 刊名 | Rsc advances
 |
| 出版日期 | 2016 |
| 卷号 | 6期号:92页码:89665-89670 |
| ISSN号 | 2046-2069 |
| DOI | 10.1039/c6ra16686e |
| 通讯作者 | Kang, chuanqing(kangcq@ciac.ac.cn) |
| 英文摘要 | Excellent diastereoselectivity (dr value up to 100 : 0) was achieved in dmap-catalyzed p-n bond formation in the synthesis of p-chirogenic organophosphines from phenylphosphonic dichloride (php(o)cl-2) and (s)-2-pyrrolidinemethanol derivatives. investigations using nmr spectroscopy and calculations revealed the formation of a bimolecular complex from (php(o)cl-2) and revealed dmap as an 'active phosphonyl' that was converted to the p-n bonded compound with a significant preference for one of two diastereomers through dynamic kinetic resolution. these results present for the first time the mechanism of conversion from an achiral phosphorus centre to a p-stereogenic centre by direct stereoselective reaction at the phosphorus centre. |
| WOS关键词 | C-H ARYLATION ; ENANTIOSELECTIVE SYNTHESIS ; STEREOGENIC PHOSPHINE ; NUCLEOPHILIC-SUBSTITUTION ; STEREOSELECTIVE-SYNTHESIS ; PHOSPHORUS-COMPOUNDS ; HYDROGENATION ; LIGANDS ; COMPLEXES ; CATALYST |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Multidisciplinary |
| 语种 | 英语 |
| WOS记录号 | WOS:000384441200086 |
| 出版者 | ROYAL SOC CHEMISTRY |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2374919 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Kang, Chuanqing |
| 作者单位 | 1.Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Northeast Normal Univ, Fac Chem, Changchun 130024, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Lanlan,Cao, Shanshan,Du, Zhijun,et al. 4-dimethylaminopyridine-catalyzed dynamic kinetic resolution in asymmetric synthesis of p-chirogenic 1,3,2-oxazaphospholidine-2-oxides[J]. Rsc advances,2016,6(92):89665-89670. |
| APA | Wang, Lanlan.,Cao, Shanshan.,Du, Zhijun.,Wu, Qiang.,Bian, Zheng.,...&Zhang, Jingping.(2016).4-dimethylaminopyridine-catalyzed dynamic kinetic resolution in asymmetric synthesis of p-chirogenic 1,3,2-oxazaphospholidine-2-oxides.Rsc advances,6(92),89665-89670. |
| MLA | Wang, Lanlan,et al."4-dimethylaminopyridine-catalyzed dynamic kinetic resolution in asymmetric synthesis of p-chirogenic 1,3,2-oxazaphospholidine-2-oxides".Rsc advances 6.92(2016):89665-89670. |
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来源：中国科学院大学
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