Synthesis of heteroarylated ketones via bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic enones and dienones
| Autor: | Mingwan Leng, Levi M. Stanley, Tanner L. Metz, Joshua Evans |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Indole test
Steric effects 010405 organic chemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Furan Drug Discovery Thiophene Trifluoromethanesulfonate Pyrrole |
| Zdroj: | Tetrahedron. 74:3283-3292 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2018.04.002 |
| Popis: | The development and optimization of bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic, β,β-disubstituted enones and dienones is described. Additions of a range of heteroarenes, including furan, thiophene, pyrrole, and indole nucleophiles, to cyclic, β,β-disubstituted enones occur to form all-carbon quaternary centers in up to 88% yield. In addition, regioselective 1,6-additions of electron-rich heteroarenes to 3-vinyl-2-cyclohexenone occur to produce a variety of δ-heteroarylated, β,β-disubstituted enones in up to 93% yield. The high 1,6-selectivity for these reactions is attributed to the increased steric bulk at the β-position relative to the δ-position, and no competing 1,4-conjugate addition is observed. |
| Databáze: | OpenAIRE |
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