期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 32, 页码 5386-5392出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600850
关键词
Helical structures; Synthetic methods; Cycloaddition; Sulfur heterocycles; Diastereoselectivity; Quinones
资金
- Istituto Toscano Tumori (ITT)
The reaction of transient ortho-thioquinones, which act as electron-poor dienes, with properly designed bis-dienophiles leads to the formation of helical-shaped bis-benzoxathiine cycloadducts with complete control of the regiochemistry and the relative stereochemistry. Bis-benzoxathiines were the result of two consecutive inverse-electron-demand cycloaddition processes with stereospecific approach of the diene anti to the bis-dienophile. The helical-shaped structure of the final products was demonstrated spectroscopically and confirmed by single-crystal X-ray analysis.
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