Tandem Acyl Substitution/Michael Addition of Thioesters with Vinylmagnesium Bromide
| Autor: | Vera Hirschbeck, Ivana Fleischer, Marlene Böldl, Paul H. Gehrtz |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Reaction conditions Ketone Tandem 010405 organic chemistry Chemistry Organic Chemistry Nucleophilic acyl substitution 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Cascade reaction Bromide Michael reaction Molecule Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 21:2578-2582 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b00538 |
| Popis: | A tandem reaction of thioesters with vinylmagnesium bromide is reported. The initial acyl substitution provides an α,β-unsaturated ketone which further reacts with the liberated thiolate. This transition-metal-free synthesis of β-sulfanyl ketones takes place under mild reaction conditions, whereas the addition of a second Grignard molecule is almost completely suppressed. The carefully chosen parameters enabled the transformation of different substrates in moderate to good yields. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|