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DOI | 10.1126/science.aaw4029 |
Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines | |
Zhang, Shaochen1; del Pozo, Juan1; Romiti, Filippo1,2; Mu, Yucheng1; Torker, Sebastian1,2; Hoveyda, Amir H.1,2 | |
2019-04-05 | |
发表期刊 | SCIENCE |
ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 364期号:6435页码:45-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA; France |
英文摘要 | Accessing enantiomerically enriched amines often demands oxidation-state adjustments, protection and deprotection processes, and purification procedures that increase cost and waste, limiting applicability. When diastereomers can be formed, one isomer is attainable. Here, we show that nitriles, largely viewed as insufficiently reactive, can be transformed directly to multifunctional unprotected homoallylic amines by enantioselective addition of a carbon-based nucleophile and diastereodivergent reduction of the resulting ketimine. Successful implementation requires that competing copper-based catalysts be present simultaneously and that the slower-forming and less reactive one engages first. This challenge was addressed by incorporation of a nonproductive side cycle, fueled selectively by inexpensive additives, to delay the function of the more active catalyst. The utility of this approach is highlighted by its application to the efficient preparation of the anticancer agent (+)-tangutorine. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000463585700030 |
WOS关键词 | DENSITY FUNCTIONALS ; OLEFIN METATHESIS ; STEREOSELECTIVE-SYNTHESIS ; ALLYLIC ALCOHOLS ; BASIS-SETS ; ALLYLATION ; IMINES ; DISPERSION ; EFFICIENT ; THERMOCHEMISTRY |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/201124 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA; 2.Univ Strasbourg, Supramol Sci & Engn Inst, F-67000 Strasbourg, France |
推荐引用方式 GB/T 7714 | Zhang, Shaochen,del Pozo, Juan,Romiti, Filippo,et al. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines[J]. SCIENCE,2019,364(6435):45-+. |
APA | Zhang, Shaochen,del Pozo, Juan,Romiti, Filippo,Mu, Yucheng,Torker, Sebastian,&Hoveyda, Amir H..(2019).Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines.SCIENCE,364(6435),45-+. |
MLA | Zhang, Shaochen,et al."Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines".SCIENCE 364.6435(2019):45-+. |
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