β-Silyl-Assisted Tandem Diels-Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones
| Autor: | Wesley A. Chalifoux, Punyanuch Sophanpanichkul, Rachael A. Carmichael |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Annulation
Trimethylsilyl Tandem Silylation 010405 organic chemistry Aryl Organic Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Cascade reaction Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 19(10) |
| ISSN: | 1523-7052 |
| Popis: | A one-pot tandem Diels–Alder/Nazarov reaction of 1-aryl-3-(trimethylsilyl) ynones has been achieved to generate carbo- and heterocyclic fused ring systems in good to excellent yields. The β-silyl effect is instrumental in accessing this otherwise challenging cascade annulation reaction. The tandem reaction proceeds in the presence of BCl3 to generate three new carbon–carbon bonds, a quaternary carbon, and two stereogenic centers with excellent diastereocontrol. A variety of substituted arenes, and even heteroaromatics, are tolerated to provide tricyclic products that are of interest as advanced intermediates toward biologically relevant compounds. |
| Databáze: | OpenAIRE |
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