GSTDTAP  > 地球科学
DOI10.1126/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
ISSN0036-8075
EISSN1095-9203
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
被引频次:153[WOS]   [WOS记录]     [WOS相关记录]
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
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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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