Design, synthesis, and applications of stereospecific 1,3-diene carbonyls

被引:0
作者
Qiang Feng [1 ]
Shihui Wang [1 ]
Xingxing Ma [2 ]
Changqing Rao [1 ]
Qiuling Song [1 ,2 ,3 ]
机构
[1] Institute of Next Generation Matter Transformation, College of Material Sciences & Engineering, Huaqiao University
[2] Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, Fuzhou University
[3] School of Chemistry and Chemical Engineering, Henan Normal University
关键词
D O I
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中图分类号
O621.3 [有机合成化学];
学科分类号
070303 ; 081704 ;
摘要
The strategy toward the synthesis of various 1,3-dienals or 1,3-dienones is disclosed between diazo compounds and furans,which features metal-free, additive-free, broad functional group tolerance, and readily accessible starting materials. Notably, this strategy is applicable in both intramolecular and intermolecular protocols. Mechanistic studies suggested that the reactions undergo a cyclopropanation/rearrangement sequence. With an E/E-1,3-dienal, corresponding N-tosylhydrazones were readily prepared and subjected to phenylboronic acid to form a double bond migration product and indoles to construct a five-member ring via [3 + 2] annulation reaction.
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页码:912 / 917
页数:6
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