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DOI | 10.1126/science.aat5883 |
Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement | |
Kaldre, Dainis; Klose, Immo; Maulide, Nuno | |
2018-08-17 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2018 |
卷号 | 361期号:6403页码:664-667 |
文章类型 | Article |
语种 | 英语 |
国家 | Austria |
英文摘要 | The chemistry of the carbonyl group is essential to modern organic synthesis. The preparation of substituted, enantioenriched 1,3- or 1,5-dicarbonyls is well developed, as their disconnection naturally follows from the intrinsic polarity of the carbonyl group. By contrast, a general enantioselective access to quaternary stereocenters in acyclic 1,4-dicarbonyl systems remains an unresolved problem, despite the tremendous importance of 2,3-substituted 1,4-dicarbonyl motifs in natural products and drug scaffolds. Here we present a broad enantioselective and stereodivergent strategy to access acyclic, polysubstituted 1,4-dicarbonyls via acid-catalyzed [3,3]-sulfonium rearrangement starting from vinyl sulfoxides and ynamides. The stereochemistry at sulfur governs the absolute sense of chiral induction, whereas the double bond geometry dictates the relative configuration of the final products. |
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:000442818200035 |
WOS关键词 | QUATERNARY STEREOGENIC CENTERS ; DUAL CATALYSIS ; ALPHA-ALLYLATION ; DIASTEREODIVERGENT ; SULFOXIDES ; CARBON ; TRIFLUOROMETHYLATION ; CONSTRUCTION ; INHIBITORS ; MOLECULES |
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/199377 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | Univ Vienna, Inst Organ Chem, Wahringer Str 38, A-1090 Vienna, Austria |
推荐引用方式 GB/T 7714 | Kaldre, Dainis,Klose, Immo,Maulide, Nuno. Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement[J]. SCIENCE,2018,361(6403):664-667. |
APA | Kaldre, Dainis,Klose, Immo,&Maulide, Nuno.(2018).Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement.SCIENCE,361(6403),664-667. |
MLA | Kaldre, Dainis,et al."Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement".SCIENCE 361.6403(2018):664-667. |
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