Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates
| Autor: | Kornkamon Akkarasereenon, Poonsakdi Ploypradith, Somsak Ruchirawat, Kassrin Tangdenpaisal |
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| Rok vydání: | 2020 |
| Předmět: |
Olefin fiber
010405 organic chemistry Organic Chemistry 010402 general chemistry Metathesis 01 natural sciences Biochemistry Medicinal chemistry Cycloaddition 0104 chemical sciences Quinone Benzyl acetate chemistry.chemical_compound chemistry Cinnamates Physical and Theoretical Chemistry Brønsted–Lowry acid–base theory Selectivity |
| Zdroj: | Organic & Biomolecular Chemistry. 18:8854-8866 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | ortho-Quinone methides (o-QMs) generated from the corresponding benzyl acetate precursors chemoselectively underwent the formal [4 + 2]-cycloadditions with the olefin of styrene, stilbene, or cinnamate derivatives by using different transition metal salts or Bronsted acids. Such selectivity was obtained when these olefins either separately acted as the dienophiles or were simultaneously present on the same dienophiles. Complete selectivity was also achieved between the stilbene olefin and acetylene to furnish the key chroman intermediate for the subsequent ring-closing metathesis (RCM), affording the corresponding tetracyclic 5H-dihydronaphtho[1,2-c]chromene. |
| Databáze: | OpenAIRE |
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